[ CAS No. 37813-30-2 ]

Name: Boc-Hyp-OEt
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Quality Control of [ 37813-30-2 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 37813-30-2 ]

CAS No. :	37813-30-2	MDL No. :	MFCD09264314
Formula :	C₁₂H₂₁NO₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	259.30	Pubchem ID :	12709318
Synonyms :

Computed Properties of [ 37813-30-2 ]

TPSA :Topological Polar Surface Area	76.1	H-Bond Acceptor Count :	5
XLogP3 :	0.9	H-Bond Donor Count :	1
SP3 :	0.83	Rotatable Bond Count :	5

Safety of [ 37813-30-2 ]

Signal Word:	Warning	Class	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 37813-30-2 ]

Upstream synthesis route of [ 37813-30-2 ]
Downstream synthetic route of [ 37813-30-2 ]

[ 37813-30-2 ] Synthesis Path-Upstream 1~11

1
[ 24424-99-5 ]
[ 33996-30-4 ]
[ 37813-30-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine In ethanol; dichloromethane at 0 - 20℃; for 16.25 h;	Step 2:To a solution of compound 2 (HCI salt, 146.2 g, 0.747 mol) dissolved in CH₂CI₂ (1600 ml) and EtOH (100 ml) and cooled to 0 ⁰C was added Et₃N (113.4 g, 1.12 mol, 156.2 ml). t-BOC anhydride (195.6, 0.90 mol) was added portion-wise. The reaction mixture was stirred at 0 ⁰C for 15 min, then at RT for 16 h. The resulting mixture was concentrated to ~ 800 ml volume and washed with water. The organic solution was dried (MgSO₄), filtered, and concentrated. Purification by silica gel chromatography (eluant: 20percent EtOAc - CH₂CI₂) gave the product 3 (193.7 g, 100percent) as a yellow oil. MS (M+Na): m/e 282. ¹H-NMR (CDCI₃) δ 1.30 (t, 3H)₁ 1.45 (s, 9H), 1.75 (m, 1 H), 2.10 (m, 1 H), 2.30 (m, 1 H), 3.45 and 3.55 (d, 1 H for two rotamers), 3.65 (dd, 1 H), 4.25 (m, 2H), 4.40 and 4.45 (t, 1H for two rotamers), 4.55 (broad s, 1 H).
100%	With triethylamine In ethanol; dichloromethane at 0 - 20℃;	Step 2:To a solution of compound 2 (HCl salt, 146.2 g, 0.747 mol) dissolved in CH₂Cl₂(1600 ml) and EtOH (100 ml) and cooled to 0° C. was added Et₃N (113.4 g, 1.12 mol, 156.2 ml). t-BOC anhydride (195.6, 0.90 mol) was added portionwise. The reaction mixture was stirred at 0° C. for 15 min, then at RT for 16 h. The resulting mixture was concentrated to 800 ml volume and washed with water. The organic solution was dried (MgSO₄), filtered, and concentrated. Purification by silica gel chromatography (eluant: 20percent EtOAc-CH₂Cl₂) gave the product 3 (193.7 g, 100percent) as a yellow oil. MS (M+Na): m/e 282. ¹H-NMR (CDCl₃) δ 1.30 (t, 3H), 1.45 (s, 9H), 1.75 (m, 1H), 2.10 (m, 1H), 2.30 (m. 1H), 3.45 and 3.55 (d, 1H for two rotamers), 3.65 (dd, 1H), 4.25 (m, 2H), 4.40 and 4.45 (t, 1H for two rotamers), 4.55 (broad s, 1H).
100%	Stage #1: With triethylamine In 1,4-dioxane; water at 0℃; for 0.17 h; Stage #2: at 20℃; for 20.00 h;	2B (13.4 g, 68.5 mmol) was dissolved in a mixed solution of 1,4-dioxane (50 mL) and water (50 mL) at room temperature and cooled to 0 ° C,Triethylamine (17.3 g, 0.171 mmol) was added and the mixture was stirred for 10 minutes.A mixture of di-tricarbonate (13.4 g, 68.5 mmol)In dichloromethane (50 mL) was added dropwise to the reaction solution and allowed to react at room temperature for 20 hours.Water (100 mL) was added to the reaction solution and extracted with dichloromethane (100 mL x 4).The organic phases were combined and washed with saturated brine solution (50 mL x 1). Dried over anhydrous magnesium sulfate,The filtrate was concentrated under reduced pressure to give pale yellow liquid 2C (18 g, yield 100percent).

Reference： [1] Patent: WO2008/8327, 2008, A2. Location in patent: Page/Page column 15-16
[2] Patent: US2011/3780, 2011, A1. Location in patent: Page/Page column 4
[3] Journal of Heterocyclic Chemistry, 2011, vol. 48, # 5, p. 1132 - 1139
[4] Patent: TW2017/8221, 2017, A. Location in patent: Page/Page column 38
[5] Synlett, 2011, # 14, p. 2059 - 2063
[6] Patent: WO2005/70934, 2005, A1. Location in patent: Page/Page column 59

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[ 61478-25-9 ]
[ 37813-30-2 ]

Yield	Reaction Conditions	Operation in experiment
74.9%	With triethylamine In ethanol; dichloromethane at 0 - 20℃;	Example 214. Synthesis of 3-fluoro-2-(4-(3-((2S,4R)-4-hydroxy-2- (hydroxymethyl)pyro-lidin-l-yl)-lH-pyrazol-l-yl)-5-oxo-6,7-dihydro-5H-pyrrolo[3,4- b]pyridin-2-yl)benzonitrile, 1-214 Synthesis of compound 214.2. To a solution of 214.1 (5.0 g, 25.6mmol, l.Oeq) in DCM (50 niL) and ethanol (10 niL) was added Et₃N (5.2 niL, 0.038 mmol, 1.5 eq) di-tert.butyl dicarbonate (032mmol, 1.2eq) at 0 °C. Reaction mixture was stirred at room temperature for 16 h. Upon completion of the reaction, mixture was transferred into water and extracted with DCM, combined organic layers were washed with brine, dried over Na₂S0₄ and concentrated under reduced pressure to obtained crude which was purified by column chromatography to furnish 214.2 . (6.1 g, 74.9 percent). MS(ES): m/z 260.12 [M+H]⁺.

Reference： [1] Patent: WO2017/40757, 2017, A1. Location in patent: Paragraph 00954-00955
[2] Tetrahedron Asymmetry, 2002, vol. 13, # 2, p. 167 - 172
[3] Angewandte Chemie - International Edition, 2009, vol. 48, # 10, p. 1784 - 1787

3
[ 13726-69-7 ]
[ 75-03-6 ]
[ 37813-30-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 12.00 h;	To a mixture of commercial (4R)-4-hydroxy-L-proline (75g, 0. 57MOL) in 10percent NAOH (11) was added (Boc) 20 (186g, 0. 855mol) at 0 C with stirring. The reaction was allowed to stir at RT for 10h and then washed with petroleum ether. The aqueous layer was acidified with citric acid to pH=4 and extracted with ethyl acetate. The combined organic layer was washed with brine and dried over NA2S04. The solvent was removed under vacuum to give crude (4R)-I-(TERT-BUTOXYCARBONYL)-4-HYDROXY-L-PROLINE (118G) as viscous liquid. Yield: 89percent To a solution of (4R)-1-(tert-butoxycarbonylo)-4-hydroxy-L-proline (100g, 0. 432MOL) in dry DMF (600ML), at 0 C was added K2CO3 (179g, 1. 3mol) followed by iodoethane (LOLG, 0. 65MOL). After stirring at RT for 12h, K2CO3 was filtered off and DMF was distilled off under reduce pressure. The residue was diluted with dichloromethane (11), washed with brine and dried. The solvent was removed under vacuum to give crude 1-1-TERT-BUTYL 2- ethyl (2S, 4R)-4-hydroxypyrrolidine-1, 2-dicarboxylate (103g) as yellow liquid. Yield: 91percent H NMR (300MHZ, CDC ) : 1.25 (t, 3H), 1.4 (d, 9H), 1.9-2. 2 (M, 2H), 2.5 (M, IH), 3.5 (M, 2H), 4.2 (M, 2H), 4.4-4. 6 (M, 2H). To a solution of 1-tert-butyl 2-ethyl (2S, 4R)-4-HYDROXYPYRROLIDINE-1, 2-dicarboxylate (100g, 0. 38MOL) in dry dichloromethane (1.51) at 25 C was added DMAP (47g, 0. 38MOL), followed by triethylamine (39g, 0. 38mol). To the above reaction mixture was added TBDMSCl (64g, 0. 42mol) dissolved in dry dichloromethane (200ML) drop-wise over a period OF 45MIN. After stirring at RT for 20H, the reaction mixture was diluted with water and separated the organic layer. The organic layer was washed with 5percent aq. citric acid, brine and dried over NA2SO4. The solvent was removed under vacuum to give I-TERT-BUTYL 2-ethyl (2S, 4R)-4- {[TERT-BUTYL (DIMETHYL) silyl] oxy} pyrrolidine-1, 2-DICARBOXYLATE (140g) as a colorless liquid. Yield: 97percent 'H NMR (300MHz, CDC13) : 0.0 (s, 6H), 0. 8 (s, 9H), 1.2 (t, 3H), 1. 45 (d, 9H), 1. 7-1. 9 (M, 2H), 2.2 (M, 1H), 3.3-3. 5 (M, 2H), 4.2 (M, 2H), 4.5 (M, 1H). To a suspension of lithium aluminium hydride (lOg) in dry tetrahydrofuran (750ml) at- 40 C was added 1-tert-butyl 2-ethyl 1-TERT-BUTYL 2-ethyl (2S,4R)-4-{[(tert- butyl (dimethyl) silyl] oxy} pyrrolidine-1, 2-dicarboxylate (100g, 0. 289mol) drop-wise in tetrahydrofuran (250ML). After stirring AT-TO C for 5H, the reaction mixture was quenched with 10percent NAOH (40ML). Filtered off the solid residue, washed with tetrahydrofuran and the filtrate was evaporated under reduce pressure to give tert-butyl (2S, 4R)-4-{[TERT- butyl (dimethyl) silyl] OXY}-2- (HYDROXYMETHYL) PYRROLIDINE-1-CARBOXYLATE (85g) as a colorless liquid. Yield: 94percent LCMS: ESI+: 232 (M-Boc+H)+, 276 (M-tBu+H) +, 354 (M+Na) + 'H NMR (300MHZ, DMSO-d6) : 0.05 (s, 6H), 0.78 (s, 9H), 1.33 (s, 9H), 1.65-2. 00 (m, 2H), 3.20 (m, 2H), 3. 38 (m, 2H), 3.70 (m, 1H), 4.30 (m, 1H), 4. 60 (t, 1H). To a mixture of DMSO (53g, 0. 68MOL) and oxalylchloride (43G, 0. 34MOL) in dry dichloromethane (1. 51) at-78oC was added tert-butyl (2S, 4R)-4-{[tert-butyl (dimethyl) silyl] OXY}-2-(HYDROXYMETHYL) PYLROLIDINE-L-CARBOXYLATE (75g, 0. 226MOL) drop-wise. After stirring at-78oC for IH, was added triethylamine (158ml, 1. 13MOL) drop-wise and warmed the reaction mixture slowly to RT. The reaction mixture was diluted with water and separated the organic layer. The organic layer was washed with brine and dried. The solvent was removed under vacuum to give tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl] OXY}-2-FORMYLPYRROLIDINE-L-CARBOXYLATE (70g) as pale yellow liquid. Yield: 94 percent

Reference： [1] Patent: WO2004/76407, 2004, A2. Location in patent: Page 27-29
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 9, p. 4030 - 4051

4
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Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 14, p. 1511 - 1514
[2] Patent: US2005/165065, 2005, A1. Location in patent: Page/Page column 21

5
[ 1070-19-5 ]
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Reference： [1] Journal of Organic Chemistry, 1981, vol. 46, # 14, p. 2954 - 2960

6
[ 41840-28-2 ]
[ 61478-25-9 ]
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Reference： [1] Journal of Organic Chemistry, 1980, vol. 45, # 23, p. 4728 - 4739

7
[ 74-96-4 ]
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Reference： [1] Chemistry Letters, 2006, vol. 35, # 3, p. 300 - 301
[2] Chemistry Letters, 2001, # 7, p. 634 - 635

8
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[ 24424-99-5 ]
[ 51-35-4 ]
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Reference： [1] Journal of Organic Chemistry, 2005, vol. 70, # 4, p. 1306 - 1315

9
[ 51-35-4 ]
[ 37813-30-2 ]

Reference： [1] Chemistry Letters, 2006, vol. 35, # 3, p. 300 - 301
[2] Tetrahedron Asymmetry, 2002, vol. 13, # 2, p. 167 - 172
[3] Chemistry Letters, 2001, # 7, p. 634 - 635
[4] Journal of Organic Chemistry, 1981, vol. 46, # 14, p. 2954 - 2960
[5] Journal of Organic Chemistry, 1980, vol. 45, # 23, p. 4728 - 4739
[6] Journal of Heterocyclic Chemistry, 2011, vol. 48, # 5, p. 1132 - 1139
[7] Patent: TW2017/8221, 2017, A
[8] Journal of Medicinal Chemistry, 2018, vol. 61, # 9, p. 4030 - 4051

10
[ 74-96-4 ]
[ 37813-30-2 ]

Reference： [1] Chemical Communications, 2004, # 10, p. 1208 - 1209

11
[ 24424-99-5 ]
[ 37813-30-2 ]

Reference： [1] Chemistry Letters, 2001, # 7, p. 634 - 635
[2] Journal of Medicinal Chemistry, 2018, vol. 61, # 9, p. 4030 - 4051

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[ 37813-30-2 ]

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
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H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 37813-30-2 ]

Quality Control of [ 37813-30-2 ]

Related Doc. of [ 37813-30-2 ]

Product Details of [ 37813-30-2 ]

Computed Properties of [ 37813-30-2 ]

Safety of [ 37813-30-2 ]

Application In Synthesis of [ 37813-30-2 ]

[ 37813-30-2 ] Synthesis Path-Upstream 1~11

[ 37813-30-2 ] Synthesis Path-Downstream 1~10

Related Functional Groups of
[ 37813-30-2 ]

Amino Acid Derivatives

Precautionary Statements-General

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[ CAS No. 37813-30-2 ]

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[ 37813-30-2 ] Synthesis Path-Upstream 1~11

[ 37813-30-2 ] Synthesis Path-Downstream 1~10

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Amino Acid Derivatives

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry(we will check your order as soon as possible)

Related Functional Groups of
[ 37813-30-2 ]