[ CAS No. 19009-39-3 ]

Name: 19009-39-3|Diisopropylcarbamoyl Chloride|98%
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SKU: A899940
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Quality Control of [ 19009-39-3 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 19009-39-3 ]

Product Details of [ 19009-39-3 ]

CAS No. :	19009-39-3	MDL No. :	MFCD00015013
Formula :	C₇H₁₄ClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	163.65 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of of [ 19009-39-3 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.86
Num. rotatable bonds :	3
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	44.04
TPSA :	20.31 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.61 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.29
Log Po/w (XLOGP3) :	2.38
Log Po/w (WLOGP) :	2.46
Log Po/w (MLOGP) :	1.96
Log Po/w (SILICOS-IT) :	0.99
Consensus Log Po/w :	2.02

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.16
Solubility :	1.14 mg/ml ; 0.00698 mol/l
Class :	Soluble
Log S (Ali) :	-2.45
Solubility :	0.584 mg/ml ; 0.00357 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.42
Solubility :	6.25 mg/ml ; 0.0382 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.19

Safety of [ 19009-39-3 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	3261
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 19009-39-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 19009-39-3 ]

[ 19009-39-3 ] Synthesis Path-Downstream 1~42

1
[ 2700-30-3 ]
[ 19009-39-3 ]

Reference： [1]Chemische Berichte,1968,vol. 101,p. 113 - 120

2
[ 19009-39-3 ]
[ 158150-20-0 ]
[ 158150-24-4 ]

Yield	Reaction Conditions	Operation in experiment
73%	With silver carbonate In toluene at 110℃; for 3h; Inert atmosphere;
73%	With silver carbonate In toluene at 110℃; for 3h;	2,3-dimethoxypyridin-4-yl diisopropylcarbamate (2l). To a solution of 2,3- dimethoxypyridin-4-ol (9) (0.30 g, l .93mmol) in toluene (10 mL) was added silver carbonate (0.80 g, 2.9 mmol) and diisopropylcarbamyl chloride (0.484 g, 2.9 mmol) and the reaction mixture was refluxed for 3 h. The suspension was allowed to cool and passed through celite washing with MeOH, removal of the solvent in vacuo and purification by chromatography (DCM:Et20 96:4) provided the title compound as a colorless oil with yield (398 mg, 73%): 1H NMR (400 MHz, CDCl3) d 1.26 (d, 12H, J = 6.8 Hz), 3.81 (s, 3H), 3.95 (s, 3H), 3.99 (m, 2H), 6.68 (d, 1H, J= 5.6 Hz), 7.77 (d, 1H, J= 5.6 Hz); 13CNMR (100 MHz, CDCl3) d 20.2, 21.0, 46.6, 53.5, 60, 112.7, 135.7 140.4, 150.8, 152.1, 158.8.
70%	With silver carbonate In toluene at 80℃; for 48h;

Reference： [1]Wang, Hezhen; Huwaimel, Bader; Verma, Kshitij; Miller, James; Germain, Todd M.; Kinarivala, Nihar; Pappas, Dimitri; Brookes, Paul S.; Trippier, Paul C. [ChemMedChem, 2017, vol. 12, # 13, p. 1033 - 1044]
[2]Current Patent Assignee: UNIVERSITY OF ROCHESTER - WO2019/217631, 2019, A1 Location in patent: Paragraph 0074; 0122
[3]Trecourt, Francois; Mallet, Marc; Mongin, Olivier; Queguiner, Guy [Journal of Organic Chemistry, 1994, vol. 59, # 21, p. 6173 - 6178]

3
[ 19009-39-3 ]
[ 697-64-3 ]
[ 616-38-6 ]
(R)-1-Diisopropylcarbamoyloxy-indan-1-carboxylic acid methyl ester [ No CAS ]
[ 256531-66-5 ]

Reference： [1]European Journal of Organic Chemistry,1999,p. 3519 - 3524
[2]European Journal of Organic Chemistry,1999,p. 3519 - 3524

4
[ 19009-39-3 ]
[ 16413-71-1 ]
[ 215438-67-8 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 7883 - 7887
[2]Tetrahedron,1999,vol. 55,p. 14161 - 14184

5
[ 19009-39-3 ]
[ 697-64-3 ]
[ 79-22-1 ]
(R)-1-Diisopropylcarbamoyloxy-indan-1-carboxylic acid methyl ester [ No CAS ]
[ 256531-66-5 ]

Reference： [1]European Journal of Organic Chemistry,1999,p. 3519 - 3524

6
[ 19009-39-3 ]
[ 124-38-9 ]
[ 697-64-3 ]
(S)-1-Diisopropylcarbamoyloxy-indan-1-carboxylic acid [ No CAS ]
(R)-1-Diisopropylcarbamoyloxy-indan-1-carboxylic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,1999,p. 3519 - 3524

7
[ 75-77-4 ]
[ 19009-39-3 ]
[ 697-64-3 ]
Diisopropyl-carbamic acid (R)-1-trimethylsilanyl-indan-1-yl ester [ No CAS ]
Diisopropyl-carbamic acid (S)-1-trimethylsilanyl-indan-1-yl ester [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,1999,p. 3519 - 3524

8
[ 4238-71-5 ]
[ 19009-39-3 ]
[ 759-65-9 ]
2-(1-benzyl-1<i>H</i>-imidazol-2-yl)-2-diisopropylcarbamoyloxy-3-methyl-succinic acid diethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 68h;

Reference： [1]Hlasta, Dennis J. [Organic Letters, 2001, vol. 3, # 2, p. 157 - 159]

9
[ 19009-39-3 ]
[ 619-60-3 ]
4-(dimethylamino)phenyl N,N-diisopropyl carbamate [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2000,p. 3232 - 3249

10
[ 1759-28-0 ]
[ 19009-39-3 ]
[ 100-52-7 ]
diisopropyl-carbamic acid (4-methyl-5-vinyl-thiazol-2-yl)-phenyl-methyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 189 - 192

11
[ 872-49-1 ]
[ 19009-39-3 ]
[ 100-52-7 ]
diisopropyl-carbamic acid (5-chloro-1-methyl-1<i>H</i>-imidazol-2-yl)-phenyl-methyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 189 - 192

12
[ 3219-63-4 ]
[ 19009-39-3 ]
(trimethylsilyl)methyl N,N-diisopropylcarbamate [ No CAS ]

Reference： [1]Synthesis,2004,p. 2704 - 2710

13
[ 75-80-9 ]
[ 19009-39-3 ]
2,2,2-tribromoethyl N,N-diisopropylcarbamate [ No CAS ]

Reference： [1]Organic Letters,2002,vol. 4,p. 2193 - 2195
[2]Journal of Fluorine Chemistry,2006,vol. 127,p. 476 - 488

14
[ 19009-39-3 ]
[ 153199-54-3 ]
[ 437709-73-4 ]

Reference： [1]Journal of Organic Chemistry,2002,vol. 67,p. 3272 - 3276

15
[ 19009-39-3 ]
[ 50919-06-7 ]
[ 549503-57-3 ]

Reference： [1]Advanced Synthesis and Catalysis,2003,vol. 345,p. 185 - 189

16
[ 19009-39-3 ]
[ 34068-01-4 ]
1-(3-benzyloxyphenyl)vinyl N,N-diisopropylcarbamate [ No CAS ]

Reference： [1]Synlett,2007,p. 2420 - 2424

17
[ 19009-39-3 ]
[ 3279-07-0 ]
C₁₇H₂₆N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92.1%	With pyridine; triethylamine; In acetonitrile; at 60℃; for 5h;	Example 1-1: Synthesis of Exemplified compound (1) The compound was synthesized in accordance with following reaction scheme. [] Into 50 mL of acetonitrile were dissolved 5.80 g (29.7 mmol) of <strong>[3279-07-0]4-t-butyl-2-nitrophenol</strong> and 5.00 g (30.6 mmol) of N,N-diisopropylcarbamoyl chloride, and then, to the resultant solution, were added 4.8 mL of triethylamine and 1.0 mL of pyridine. The resultant solution was stirred at 60 C for 5 hours. To the reaction solution were added ethyl acetate and water, to extract the reaction product. The organic phase was washed with each of 0.1N potassium carbonate aqueous solution, diluted hydrochloric acid, and saturated brine, followed by drying over anhydrous magnesium sulfate. The result was filtered and then the solvent was distilled off under reduced pressure. The remaining product was purified by silica gel chromatography, using a mixed solvent of ethyl acetate and hexane as an eluent, to yield 8.82 g (27.4 mmol) of Exemplified compound (1A), as a light yellow crystal. Yield: 92.1%.

Reference： [1]Patent: EP1516870,2005,A1 .Location in patent: Page/Page column 22; 23

18
[ 19009-39-3 ]
[ 42969-65-3 ]
[ 900160-95-4 ]

Yield	Reaction Conditions	Operation in experiment
48%	With copper(l) iodide; triethylamine; triphenylphosphine;bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 57℃;	Example 4 - Preparation of 10D via Method A(R)-B To 22 g (314 mmol) of (R)-3-butyne-2-ol is added 1.62 g (8.51 mmol) ofCuI, 2.0 g (7.62 mmol) of PPh3, 3.05 g of (4.33 mmol Pd(PPh3)2CI2), 46.7 g (285 mmol) of diisopropylcarbamoyl chloride, 20OmL of THF and 120 mL of triethylamine. The mixture is heated to 570C and maintained at this temperature overnight. The solution is cooled to room temperature, filtered through a pad of celite and concentrated to an oil. The purity of this oil is 42.6% and the yield is48%. 1H-NMR (CDCI3, 400 MHz) delta 4.65 (q, 1 H, J = 6.7Hz ), 4.55 (m, 1 H), 4.16 EPO <DP n="31"/>(m, 1 H), 3.60 (m, 1 H), 1.50 (d, 3H, J = 6.7 Hz), 1.35 (d, 6H, J = 6.8Hz), 1.23 (d, 6H, J = 6.8Hz).

Reference： [1]Patent: WO2006/76452,2006,A2 .Location in patent: Page/Page column 29; 30

19
1 N-HCl [ No CAS ]
[ 19009-39-3 ]
[ 50919-06-7 ]
[ 549503-57-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With pyridine;	(b) Synthesis of 2-(2-fluorophenyl)ethyl Diisopropylcarbamate Under a nitrogen atmosphere, a mixture of 8.0 g (57.1 mmol) of <strong>[50919-06-7]2-(2-fluorophenyl)ethanol</strong>, 9.34 g (57.1 mmol) of diisopropylcarbamoyl chloride and 6.93 ml (85.7 mmol) of pyridine was heated to 90 C. and stirred overnight. After cooling to room temperature, the mixture was treated with 1 N-HCl, extracted 3 times with ethyl acetate, washed with water, saturated NaHCO3, water and brine and then dried over sodium sulfate. After the solvent was distilled off, purification of the residue by silica gel chromatography gave 14.0 g of the title compound. (Yield: 98%). 1H NMR (CDCl3): delta 1.14 (12H, d, J=6.8 Hz), 3.01 (2H, t, J=6.8 Hz), 3.50-4.20 (2H, m), 4.31 (2H, t, J=6.8 Hz), 6.95-7.30 (4H, m); EI-MS: m/z 267 (M)+

Reference： [1]Patent: US2003/144139,2003,A1

20
[ 19009-39-3 ]
[ 767-90-8 ]
[ 1086338-61-5 ]

Reference： [1]Synthesis,2008,p. 2905 - 2918

21
[ 19009-39-3 ]
[ 1142947-96-3 ]
[ 1142947-15-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With triethylamine In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; for 0.5h;	150 To a solution of 88 (46 mg, 0.1 mmol) in 2 mL of anhydrous DMF was added one drop of Et3N, followed by neat diisopropylcarbamyl chloride (20 mg, 0.12 mmol) in anhydrous TηF (33 mg in 1 mL). The reaction mixture was stirred at ambient temperature for 30 min, then filtered through 0.2 u syringe filter and purified by reverse-phase preparative ηPLC in CH3CN/H2O system containing 0.1% of TFA. Fractions, containing the product, were combined and poured into EtOAc (50 mL). The solution was treated with saturated aqueous NaHCO3 (2 x 10 mL), washed with brine (2 x 10 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo to give the title compound as a bright- yellow solid (57 mg, 97% yield).[0421] 1H NMR (500 MHz, DMSO-J6): δ 1.24 (d, J = 6.6 Hz, 12H), 1.73 (br s, 4H), 2.66 (br s, 4H), 2.90 (br s, 2H), 2.93 (t, J = 5.2 Hz, 2H), 3.35 (t, J = 5.5 Hz, 2H), 3.67 (septet, J = 6.7 Hz, 2H), 4.07 (t, J = 5.8 Hz, 2H), 4.17 (s, 2H), 6.83 (dd, J = 3.6, 1.8 Hz, IH), 6.88 (d, J = 9.1 Hz, 2H), 7.24 (dd, J = 3.4, 2.4 Hz, IH), 7.76 (d, J = 9.1 Hz, 2H), 7.85 (s, IH), 8.98 (s, IH),11.54 (s, IH)MS (ES+): m/z 588 (M+H)+

Reference： [1]Current Patent Assignee: SANOFI - WO2009/49028, 2009, A1 Location in patent: Page/Page column 178

22
[ 19009-39-3 ]
[ 613-87-6 ]
[ 1201898-70-5 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 6145 - 6149
Angew. Chem.,2014,vol. 126,p. 6259 - 6263,5
[2]Tetrahedron,2009,vol. 65,p. 9956 - 9960
[3]Angewandte Chemie - International Edition,2010,vol. 49,p. 5142 - 5145
[4]Angewandte Chemie - International Edition,2011,vol. 50,p. 1080 - 1083

23
[ 19009-39-3 ]
[ 1594-58-7 ]
[ 1206768-71-9 ]

Reference： [1]Journal of Heterocyclic Chemistry,2009,vol. 46,p. 1271 - 1279

24
[ 19009-39-3 ]
[ 1594-57-6 ]
[ 1206768-72-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,2009,vol. 46,p. 1271 - 1279

25
[ 19009-39-3 ]
[ 171032-87-4 ]
[ 1240815-56-8 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 5142 - 5145

26
[ 19009-39-3 ]
[ 1256451-72-5 ]
[ 1256451-95-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: C₁₅H₃₄OSi₂ With N,N,N,N,N,N-hexamethylphosphoric triamide; sec.-butyllithium In tetrahydrofuran; pentane at -78℃; for 0.0833333h; Inert atmosphere; Stage #2: N,N-diisopropylcarbamoyl chloride In tetrahydrofuran; pentane at -78 - 20℃; for 4h; Inert atmosphere;
92%	Stage #1: C₁₅H₃₄OSi₂ With N,N,N,N,N,N-hexamethylphosphoric triamide; sec.-butyllithium In tetrahydrofuran; pentane at -78℃; for 0.0833333h; Inert atmosphere; Stage #2: N,N-diisopropylcarbamoyl chloride In tetrahydrofuran; pentane at -78℃; for 0.25h; Inert atmosphere;	4.3. General procedure for the synthesis of 3,3-bissilyl enol derivatives in Table 4 General procedure: To a solution of 1a (86 mg, 0.3 mmol) in anhyd THF (1.5 mL) and anhyd HMPA (64 μL, 0.36 mmol) under argon was added s-BuLi (0.45 mL of a 1.0 M solution in pentane, 0.45 mmol) at -78 °C. After stirring for 5 min, triethylsilyl chloride (135 mg, 0.9 mmol) was added and the resulting solution stirred at -78 °C for another 15 min. Then the reaction was quenched with satd aq NaHCO3 (3.0 mL) and extracted with Et2O (2×5 mL). The combined organic phases were dried over Na2SO4 and concentrated under reduced pressure. Purification of the crude residue via silica gel flash column chromatography (gradient eluent: 5-10% of EtOAc/petroleum ether) afforded pure 4a (114 mg, 95%) of as a colorless oil.

Reference： [1]Song, Zhenlei; Lei, Zheng; Gao, Lu; Wu, Xia; Li, Linjie [Organic Letters, 2010, vol. 12, # 22, p. 5298 - 5301]
[2]Gan, Zubao; Wu, Ya; Gao, Lu; Sun, Xianwei; Lei, Jian; Song, Zhenlei; Li, Linjie [Tetrahedron, 2012, vol. 68, # 34, p. 6928 - 6934]

27
[ 19009-39-3 ]
[ 135-19-3 ]
[ 61912-15-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	With sodium hydride In tetrahydrofuran at 20℃; for 12h; Sealed tube;	3. General Procedure for the Preparation of Starting Materials General procedure: A solution of naphthalen-2-ol (4.3 g, 30 mmol) in dry THF (15 mmol) was addeddropwise to a suspension of NaH (60% oil dispersion, 1.3 g, 33 mmol) in dry THF (15mL) at 0 °C, and the resulting mixture was stirred at room temperature for 10 min.Diisopropylcarbamoyl chloride (5.4 g, 33 mmol) was then added to he reaction, and theresulting mixture was stirred at room temperature for 12 h. The reaction mixture wasthen cooled to 0 °C and quenched by the addition of EtOH. The solvent was removed invacuo to give a residue, which was dissolved in EtOAc and filtered through a pad ofsilica gel. The filtrate was then concentrated in vacuo to give the crude product, whichwas purified by flash column chromatography over silica gel (eluent: hexane/EtOAc =10/1) to give naphthalen-2-yl diisopropylcarbamate (10, 7.3g, 89%) as a white solid.1H NMR (CDCl3, 400 MHz): 1.32 (bs, 6H), 1.39 (bs, 6H), 4.00 (bs, 1H), 4.15 (bs, 1H),7.29 (dd, J = 2.2, 8.6 Hz, 1H), 7.41-7.49 (m, 2H), 7.58 (d, J = 2.4 Hz, 1H), 7.78-7.84(m, 3H).13C NMR (CDCl3, 100 MHz): 20.4, 21.5, 46.0, 46.9, 118.3, 121.7, 125.1, 126.2, 127.4,127.6, 129.0, 131.0, 133.8, 149.0, 153.9.
	With triethylamine In dichloromethane for 24h; Inert atmosphere; Reflux;
	In pyridine Inert atmosphere; Reflux;

Reference： [1]Nakamura, Keisuke; Yasui, Kosuke; Tobisu, Mamoru; Chatani, Naoto [Tetrahedron, 2015, vol. 71, # 26-27, p. 4484 - 4489]
[2]Matthew, Smitha C.; Glasspoole, Ben W.; Eisenberger, Patrick; Crudden, Cathleen M. [Journal of the American Chemical Society, 2014, vol. 136, # 16, p. 5828 - 5831]
[3]Antenucci, Achille; Blangetti, Marco; Bolzoni, Paola; De Nardi, Federica; Ghinato, Simone; Prandi, Cristina [Chemistry - A European Journal, 2022]

28
[ 24621-61-2 ]
[ 19009-39-3 ]
(S)-3-hydroxybutyl diisopropylcarbamate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 9846 - 9850,5
Angew. Chem.,2014,vol. 126,p. 10004 - 10008,5
Angewandte Chemie,2014,vol. 126,p. 10004 - 10008,5

29
[ 582-60-5 ]
[ 19009-39-3 ]
N,N-diisopropyl-5,6-dimethyl-1H-benzo[d]imidazole-1-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%		Following Example 3,5,6-Dimethylbenzimidazole (14.6 g, 100 mmol) was dissolved in anhydrous THF (230 mL) and transferred dropwise to the THF (150 mL) solution containing 1.2 equiv of NaH (60% in mineral oil, 4.8 g, 120 mmol) at 0 C. (Note: NaH was pre-washed with dry hexane, 10 mL x 3, under nitrogen). The mixture was stirred for 1 h at room temperature. Then, 1.1 equiv of N,N-diisopropylcarbamoylchloride (18.0 g, 110 mmol) was added directly to the reaction and the mixture was refluxed for 1 h and stirred at room temperature for overnight. Solvent was removed under reduced pressure. Ethyl acetate (~500 mL) and water (~200 mL) was added to the mixture and the aqueous phase was separated. The organic phase was further washed with brine (~100 mL x 3), and dried by Na2SO4 and concentrated. The concentrated mixture was applied to 2 x 2 inch silica pad and eluted with ethyl acetate. After the solvent was removed under vacuum, the pale yellow powder (1c) (25.2g, 92%) was obtained after re-crystallization from ethyl acetate/hexane. Melting point: 117.1-119.5C; 1H NMR (400 MHz, CDCl3) delta 1.44 (d, J = 6.8Hz, 12H), 2.41 (d, J = 2.8 Hz, 6H), 3.79-3.86 (m, 2H), 7.41 (s, 1H), 7.58 (s, 1H), 7.95 (s, 1H); 13C NMR (100MHz, CDCl3) delta 20.0, 20.3, 20.8, 48.8, 112.2, 120.1, 130.9, 132.1, 133.5, 139.4, 141.5, 149.7; IR (cm-1) 2971.93, 1681.36, 1496.99, 1433.01, 1345.52, 1304.23, 1248.68, 1211.19, 1144.93, 1097.41, 1044.36, 1019.94, 994.95, 909.64, 842.74, 754.86, 646.71, 616.50, 585.00, 554.32, 524.15, 433.79; MS (EI): mlz (relative intensity) 273 (M+, 42), 173 (11), 145 (26), 128 (61), 86 (100); HRMS: calcd. for C16H23N3OH+: 274.1919, found 274.1922.

Reference： [1]Patent: WO2015/39606,2015,A1 .Location in patent: Paragraph 0044

30
[ 19009-39-3 ]
[ 33689-29-1 ]
C₁₂H₂₁NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.66 g	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 2h;	To a solution of <strong>[33689-29-1]methyl 1-hydroxycyclopropanecarboxylate</strong> (0.741 mL, 8.61 mmol) was added diisopropylcarbamic chloride (1.550 g, 9.47 mmol) and DIEA (2.256 mL, 12.92 mmol) in DCM (15 mL). The resulting solution was stirred at rt for 2 h, then diluted with DCM and the organic layer was washed with 1 N HC1,water and brine, dried (Mg504), filtered and concentrated. The residue was purified via Biotage (15% to 30% EtOAc/Hex; 25 g column) to yield Cap L-9 Step a (0.66 g).

Reference： [1]Patent: WO2015/5901,2015,A1 .Location in patent: Page/Page column 533

31
[ 19009-39-3 ]
[ 90-43-7 ]
[1,1'-biphenyl]-2-yl N,N-diisopropylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydride In tetrahydrofuran at 20℃; for 12h; Sealed tube;	[1,1'-Biphenyl]-2-yl diisopropylcarbamate (18). A solution of [1,1'-biphenyl]-2-ol (1.7 g, 10 mmol) in dry THF (5 mL) was addeddropwise at 0°C to a suspension of NaH (60% oil dispersion, 520 mg, 13 mmol) in dryTHF (5 mL). The resulting mixture was stirred at room temperature for 10 min,diisopropylcarbamoyl chloride (1.6 g, 10 mmol) was then added, and the mixture wasstirred at room temperature for 12 h. The purification described in the general method,gave colorless oil (18, 3.0 g, 100%). Rf = 0.57 (hexane/EtOAc = 3/1).1H NMR (CDCl3, 400 MHz): 1.05 (d, 6.0 Hz, 6H), 1.17 (d, J = 5.6 Hz, 6H), 3.78 (bs, 1H), 3.94 (bs, 1H), 7.18 (d, J = 8.0 Hz, 1H), 7.24-7.42 (m, 8H).13C NMR (CDCl3, 100 MHz): 20.2, 20.8, 46.0, 46.4, 123.3, 125.3, 127.0, 127.9, 128.2,129.0, 130.5, 135.4, 138.1, 148.3, 153.1.S5HRMS (FAB): Calcd for C19H23NO2+H+ 298.1802, Found 298.1807.
43%	In pyridine Inert atmosphere; Reflux;

Reference： [1]Nakamura, Keisuke; Yasui, Kosuke; Tobisu, Mamoru; Chatani, Naoto [Tetrahedron, 2015, vol. 71, # 26-27, p. 4484 - 4489]
[2]Antenucci, Achille; Blangetti, Marco; Bolzoni, Paola; De Nardi, Federica; Ghinato, Simone; Prandi, Cristina [Chemistry - A European Journal, 2022]

32
[ 402-45-9 ]
[ 19009-39-3 ]
4-(trifluoromethyl)phenyl N,N-diisopropylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium hydride In tetrahydrofuran at 20℃; for 12h; Sealed tube;	3. General Procedure for the Preparation of Starting Materials A solution of naphthalen-2-ol (4.3 g, 30 mmol) in dry THF (15 mmol) was addeddropwise to a suspension of NaH (60% oil dispersion, 1.3 g, 33 mmol) in dry THF (15mL) at 0 °C, and the resulting mixture was stirred at room temperature for 10 min.Diisopropylcarbamoyl chloride (5.4 g, 33 mmol) was then added to he reaction, and theresulting mixture was stirred at room temperature for 12 h. The reaction mixture wasthen cooled to 0 °C and quenched by the addition of EtOH. The solvent was removed invacuo to give a residue, which was dissolved in EtOAc and filtered through a pad ofsilica gel. The filtrate was then concentrated in vacuo to give the crude product, whichwas purified by flash column chromatography over silica gel (eluent: hexane/EtOAc =10/1) to give naphthalen-2-yl diisopropylcarbamate (10, 7.3g, 89%) as a white solid.1H NMR (CDCl3, 400 MHz): 1.32 (bs, 6H), 1.39 (bs, 6H), 4.00 (bs, 1H), 4.15 (bs, 1H),7.29 (dd, J = 2.2, 8.6 Hz, 1H), 7.41-7.49 (m, 2H), 7.58 (d, J = 2.4 Hz, 1H), 7.78-7.84(m, 3H).13C NMR (CDCl3, 100 MHz): 20.4, 21.5, 46.0, 46.9, 118.3, 121.7, 125.1, 126.2, 127.4,127.6, 129.0, 131.0, 133.8, 149.0, 153.9.
	In pyridine Inert atmosphere; Reflux;

33
[ 86-79-3 ]
[ 19009-39-3 ]
9H-carbazol-2-yl diisopropylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With pyridine; for 12h;Reflux; Sealed tube;	9H-Carbazol-2-ol (3.7 g, 20 mmol) and diisopropylcarbamic chloride (3.6 g, 22 mmol)were refluxed in pyridine (50 mL) for 12 h. The resulting mixture was cooled to rt andthe solvent was removed in vacuo. The purification by flash column chromatography onsilica gel (hexane/EtOAc = 2/1, Rf = 0.61) gave 9H-carbazol-2-yl diisopropylcarbamateas a white solid (3.3 g, 53%).9H-Carbazol-2-yl diisopropylcarbamate (2.1 g, 6.6 mmol) in dry THF (10 ml) wasadded dropwise at 0 C to a suspension of NaH (60 wt% oil dispersion, 400 mg, 9.9mmol) in dry THF (10 mL). The resulting mixture was stirred at room temperature for10 min, MeI (2 mL) was then added, and the mixture was stirred at room temperaturefor 16 h. The mixture was then cooled to 0 C and quenched by the addition of water(10 mL). The THF was removed in vacuo to give an aqueous residue, which wasextracted with ether (10 mL x 3). The combined extracts were then washed with brine,dried over Na2SO4 and evaporated in vacuo to give the crude product, which waspurified by recrystallization from CHCl3-hexane to give 36 as a white solid (1.9 g,90 %, 48% for 2 steps). Rf = 0.47 (hexane/EtOAc = 5/1), white solid. Mp = 117-118 C.1H NMR (CDCl3, 400 MHz): 1.32 (bs, 6H), 1.41 (bs, 6H), 3.83 (s, 3H), 4.00 (bs, 1H),4.17 (bs, 1H), 6.98 (dd, J = 2.0, 8.6 Hz, 1H), 7.20-7.25 (m, 2H), 7.39 (d, J = 8.0 Hz,1H), 7.46 (t, J = 8.4 Hz, 1H), 8.04 (t, J = 8.2 Hz, 2H).13C NMR (CDCl3, 150 MHz): 20.5, 21.6, 29.2 46.0, 46.9, 102.1, 108.3, 113.2, 119.0,119.99, 120.02, 120.5, 122.6, 125.2, 141.4, 141.5, 150.0, 154.3.HRMS (EI): Calcd for C20H24N2O2 324.1838, Found 324.1848.

Reference： [1]Tetrahedron,2015,vol. 71,p. 4484 - 4489

34
[ 19009-39-3 ]
[ 590417-81-5 ]
C₁₆H₂₄FNO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine

Reference： [1]Roesner, Stefan; Blair, Daniel J.; Aggarwal, Varinder K. [Chemical Science, 2015, vol. 6, # 7, p. 3718 - 3723]

35
[ 19009-39-3 ]
[ 225920-05-8 ]
(S)-1-(3,5-bis(trifluoromethyl)phenyl)ethyl diisopropylcarbamate [ No CAS ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 5289 - 5292

36
[ 19009-39-3 ]
[ 100-49-2 ]
C₁₄H₂₇NO₂ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 12285 - 12289
Angew. Chem.,2016,vol. 128,p. 12473 - 12477,5

37
[ 19009-39-3 ]
[ 186507-11-9 ]
(E)-3-(3-(4-methoxyphenyl)acryloyl)phenyl N,N-diisopropylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91.7%	With pyridine; potassium carbonate In water; ethyl acetate at 70℃; for 24h;	27 Synthesis of the product (E) -3- (3- (4-methoxyphenyl) acryloyl) phenyl diisopropylcarbamate (compound of the chemical formula 23) (0.10 g, 0.4 mmol) of intermediate N1,(0.10 g, 0.785 mmol) K2CO3 / 1.5 H2O,(0.01 g, 0.215 mmol) in anhydrous K2CO3 and 5 drops of pyridine were stirred well in an appropriate amount of ethyl acetate,Heated to 70 ° C;(0.98 g, 0.60 mmol) of diisopropylcarbamoyl chloride was stirred well in an appropriate amount of ethyl acetate,Was added dropwise to the above solution,70 reaction 24h,After the reaction, the same volume of water as the reaction solution was added, and the mixture was stirred at 70 ° C for 2 h. After cooling to room temperature,The organic phase was washed twice with 2 wt% sulfuric acid and water, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give 140 mg of the product as a brown oil in 91.7% yield.
91.7%	With pyridine; potassium carbonate sesquihydrate; potassium carbonate In ethyl acetate at 70℃;	6 2.5. General procedure for the synthesis of compounds 9-12, 22, and 23 General procedure: A suspension of B1 or B2 (0.47 mmol), K2CO3/1.5H2O (0.369 mmol) and K2CO3 (0.101 mmol) in appropriate ethyl acetate was added 4 drops pyridine. The mixture was stirred and heated to 70 °C. Acyl chloride (0.705 mmol) in appropriate ethyl acetate was added dropwise. Then the reaction was stirred at 70 °C, the reaction was monitored by TLC. Upon completion, an equal volume of water was added to the mixture, stirred at 70 °C for 1.5 h. The reaction was cooled and the aqueous layer was separately washed 2* with 2% H2SO4 and water, then the combined organics were dried over MgSO4, filtered, and concentrated in vacuo to give the desired product.

Reference： [1]Current Patent Assignee: South China University of Technology; Wang, Ling; Tan, Wen; Tian, Yiguang - 2016 Location in patent: Paragraph 0240; 0241; 0242
[2]Wang, Ling; Wang, Yu; Tian, Yiguang; Shang, Jinling; Sun, Xiaoou; Chen, Hongzhuan; Wang, Hao; Tan, Wen [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 1, p. 360 - 371]

38
[ 19009-39-3 ]
[ 7287-81-2 ]
C₁₆H₂₅NO₂ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 3418 - 3422

39
[ 19009-39-3 ]
[ 1007-03-0 ]
C₁₇H₂₅NO₂ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 3418 - 3422

40
[ 19009-39-3 ]
[ 87630-36-2 ]
3-bromo-N,N-diisopropyl-1H-pyrrole-1-carboxamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 14198 - 14202
Angew. Chem.,2018,vol. 130,p. 14394 - 14398,5

41
[ 41365-75-7 ]
[ 19009-39-3 ]
N'-(3,3-diethoxypropyl)-N,N-di(propan-2-yl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With triethylamine; In benzene;	General procedure: To a solution of 2.05 g (14 mmol) of 3,3-diethoxypropan-1-amine 3 and 2.83 g (28 mmol) of triethylamine in 15 ml of benzene 14 mmol of N,N-di(alkyl, aryl)carbamoyl chloride was added dropwise at cooling (5-7 C). The reaction mixture was stirred under cooling for 2 hours. The precipitate was filtered off, the filtrate was evaporated in vacuum to give the target compound 4 as a yellow oil, which was used in subsequent reactions without further purification.

Reference： [1]Synthetic Communications,2018,vol. 48,p. 2545 - 2552

42
[ 19009-39-3 ]
[ 24034-73-9 ]
(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl diisopropylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: Geranylgeraniol With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: N,N-diisopropylcarbamoyl chloride In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 20℃; for 2.5h; Inert atmosphere;	(2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraenyl Diisopropylcarbamate (3) To a suspension of NaH (510 mg, 60% dispersion in mineral oil, washed with hexane before use, 13.2 mmol) in THF (10.0 mL) was added geranylgeraniol (2; 2.40 g, 8.26 mmol). After stirring at r.t. for30 min, a solution of N,N-diisopropylcarbamoyl chloride (1.62 g, 9.92 mmol) in THF (6.0 mL) and DMF (4.0 mL) were added successively. The reaction mixture was stirred at r.t. for 2.5 h and then treated cautiously with MeOH and H2O. The separated aqueous layer was extracted with Et2O, and the combined organic extracts were washed with brine, dried (anhyd Na2SO4), and then concentrated under reduced pressure to afford the residue (3.24 g), which was subjected to silica gel chromatography (1:10 EtOAc/hexane) to afford carbamate 3; as a colorless oil yield: 2.87 g (83%). IR (KBr): 2967, 2928, 1695, 1438, 1302, 1287, 1050 cm-1. 1H NMR (CDCl3): = 5.38 (t, J = 6.9 Hz, 1 H), 5.14-5.07 (m, 3 H), 4.60(d, J = 6.9 Hz, 2 H), 2.12-2.06 (m, 8 H), 1.98-1.95 (m, 4 H), 1.70 (s, 3H), 1.68 (s, 3 H), 1.61-1.57 (m, 11 H), 1.20 (d, J = 6.9 Hz, 12 H). 13C NMR (125 MHz, CDCl3): = 155.8, 140.7, 135.3, 134.9, 131.2,124.3, 124.1, 123.7, 119.5, 61.4, 45.9, 45.5, 39.7, 39.5, 26.7, 26.6, 26.2, 25.6, 21.1, 21.0, 17.6, 16.4, 16.0, 15.9. HRMS (ESI): m/z calcd for C27H48NO2 [M + H]+: 418.3680; found: 418.3679.

Reference： [1]Ichikawa, Yoshiyasu; Masuda, Toshiya; Morimoto, Hirofumi [Synthesis, 2019, vol. 51, # 15, p. 2959 - 2964]

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[ CAS No. 19009-39-3 ]

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[ 19009-39-3 ] Synthesis Path-Downstream 1~42

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