Z-D-Chg-OH | Ambeed.com

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Quality Control of Z-D-Chg-OH Purity: 98% SDS Specification

COA

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NMR

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HPLC

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Product Details of Z-D-Chg-OH

CAS No. :	69901-85-5
Formula :	C₁₆H₂₁NO₄
M.W :	291.34
SMILES Code :	[H][C@@](NC(=O)OCC1=CC=CC=C1)(C1CCCCC1)C(O)=O
Synonyms :	Z-D-Chg-OH
MDL No. :	MFCD00191082
InChI Key :	CUSYTUPJAYLNFQ-CQSZACIVSA-N
Pubchem ID :	14510026

Safety of Z-D-Chg-OH

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of Z-D-Chg-OH

* 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 [ 69901-85-5 ]

[ 69901-85-5 ] Synthesis Path-Downstream 1~35

1
[ 69901-85-5 ]
[ 127042-92-6 ]
[ 127042-93-7 ]

References: [1]Tetrahedron Letters,1989,vol. 30,p. 5227 - 5230.

2
[ 127042-68-6 ]
[ 69901-85-5 ]

References: [1]Tetrahedron Letters,1989,vol. 30,p. 5227 - 5230.

4
[ 69901-85-5 ]
[ 74-88-4 ]
(R)-(Benzyloxycarbonyl-methyl-amino)-cyclohexyl-acetic acid [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1984 - 2008.

5
N-(benzyloxycarbonyl)-α-dehydrocyclohexylglycine [ No CAS ]
[ 69901-75-3 ]
[ 69901-85-5 ]

References: [1]Organic Letters,2005,vol. 7,p. 3405 - 3408.

6
[ 50-00-0 ]
[ 69901-85-5 ]
[ 876366-38-0 ]

References: [1]Tetrahedron,2006,vol. 62,p. 264 - 284.

7
[ 69901-85-5 ]
(R)-(Benzyloxycarbonyl-methyl-amino)-cyclohexyl-acetic acid [ No CAS ]

References: [1]Tetrahedron,2006,vol. 62,p. 264 - 284.

8
[ 69901-85-5 ]
(R)-2-Cy-(N-3,5-diMe-C₆H₃)-2-(N-Me-N-formylamino)acetamide [ No CAS ]

References: [1]Tetrahedron,2006,vol. 62,p. 264 - 284.

9
[ 69901-85-5 ]
[ 876366-40-4 ]

References: [1]Tetrahedron,2006,vol. 62,p. 264 - 284.

10
[ 69901-85-5 ]
(R)-2-Cyclohexyl-N-(3,5-dimethyl-phenyl)-2-methylamino-acetamide; compound with formic acid [ No CAS ]

References: [1]Tetrahedron,2006,vol. 62,p. 264 - 284.

11
[ 621-84-1 ]
[ 69901-85-5 ]

References: [1]Organic Letters,2005,vol. 7,p. 3405 - 3408.

12
[ 4354-49-8 ]
[ 69901-85-5 ]

References: [1]Organic Letters,2005,vol. 7,p. 3405 - 3408.

13
[ 69901-85-5 ]
(S)-1-((R)-2-Cyclohexyl-2-methylamino-acetyl)-pyrrolidine-2-carboxylic acid [(S)-1-(benzothiazole-2-carbonyl)-4-guanidino-butyl]-amide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1984 - 2008.

14
[ 69901-85-5 ]
C₄₂H₅₃N₇O₇S₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1984 - 2008.

15
[ 69901-85-5 ]
C₄₂H₅₁N₇O₇S₂ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1984 - 2008.

16
[ 24461-61-8 ]
[ 69901-85-5 ]

References: [1]Tetrahedron Letters,1989,vol. 30,p. 5227 - 5230.

17
[ 69901-85-5 ]
[ 127042-91-5 ]

References: [1]Tetrahedron Letters,1989,vol. 30,p. 5227 - 5230.

18
[ 69901-85-5 ]
[ 127042-95-9 ]

References: [1]Tetrahedron Letters,1989,vol. 30,p. 5227 - 5230.

19
[ 69901-85-5 ]
[ 127042-94-8 ]

References: [1]Tetrahedron Letters,1989,vol. 30,p. 5227 - 5230.

20
[ 69901-85-5 ]
[ 127042-96-0 ]

References: [1]Tetrahedron Letters,1989,vol. 30,p. 5227 - 5230.

21
[ 69901-85-5 ]
[ 127042-97-1 ]

References: [1]Tetrahedron Letters,1989,vol. 30,p. 5227 - 5230.

22
[ 37763-24-9 ]
[ 69901-85-5 ]

References: [1]Tetrahedron Letters,1989,vol. 30,p. 5227 - 5230.

23
[ 501-53-1 ]
[ 69901-85-5 ]

References: [1]Tetrahedron Letters,1989,vol. 30,p. 5227 - 5230.

24
[ 69901-85-5 ]
[ 6638-79-5 ]
[ 876761-30-7 ]

Yield	Reaction Conditions	Operation in experiment
90%		Step 1. Synthesis of [(R)-Cyclohexyl-(methoxy-methyl-carbamoyl)-methyl]-carbamic acid benzyl ester To a solution of (R)-benzyloxycarbonylamino-cyclohexyl-acetic acid (25 g, 88 mmol) in DMF (100 mL) at -10 C was added HATU (36.7 g, 96 mmol, 1 .0 equiv) followed by Nu,Omicron- dimethyl hydroxyamine HCI salt (10.3 g, 105 mmol, 1 .2 equiv). To this solution was then slowly added N-methyl morpholine (28.9 mL, 263 mmol, 3.0 equiv). The internal temperature was carefully monitored. During the addition, the internal temperature rose to 0 C. The solution was stirred at 0 C for 2 hours after which the solution was diluted with EtOAc (500 mL) and washed with sat. aq. NaHC03 solution, water, 1 .0 N aq. HCI solution and brine. The organic layer was dried over Na2S04 and the solvent including DMF was removed under vacuum. The residue was diluted with EtOAc and the solution was washed with water, brine, dried (MgS04) and concentrated to give product [(R)-Cyclohexyl-(methoxy-methyl-carbamoyl)-methyl]- carbamic acid benzyl ester 26 g (yield 90 %).

References: [1]Patent: WO2012/10663,2012,A1 .Location in patent: Page/Page column 50-51.

25
[ 69901-85-5 ]
[ 876761-31-8 ]

References: [1]Patent: WO2012/10663,2012,A1 .

26
[ 69901-85-5 ]
[ 1356457-06-1 ]

References: [1]Patent: WO2012/10663,2012,A1 .

27
[ 69901-85-5 ]
[ 1240586-10-0 ]

References: [1]Patent: WO2012/10663,2012,A1 .

28
[ 69901-85-5 ]
[ 1356457-07-2 ]

References: [1]Patent: WO2012/10663,2012,A1 .

29
[ 69901-85-5 ]
[ 1356457-08-3 ]

References: [1]Patent: WO2012/10663,2012,A1 .

30
[ 69901-85-5 ]
[ 1356453-54-7 ]

References: [1]Patent: WO2012/10663,2012,A1 .

31
[ 69901-85-5 ]
[ 1356457-10-7 ]

References: [1]Patent: WO2012/10663,2012,A1 .

32
[ 69901-85-5 ]
methyl 3-(4-(3-aminophenyl)-1H-1,2,3-triazol-1-yl)propionate [ No CAS ]
(R)-methyl 3-(4-(3-(2-(((benzyloxy)carbonyl)amino)-2-cyclohexylacetamido)phenyl)-1H-1,2,3-triazol-1-yl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 40℃;Inert atmosphere; Sealed tube;	General procedure: In a typical run, a 15 mL screw cap tube was charged with the selected carboxylic acid (0.5 mmol), HATU (2 equiv/mol), DMF(1 ml) and DIPEA (2 equiv/mol.). A solution of 1 or 2 (0.5 mmol) in DMF (1 ml) was then added dropwise. The tube was flushed with argon, sealed, and the mixture was stirred overnight at 40 C. After cooling down to rt, the crude reaction mixture was diluted with water (10 mL) and extracted with EtOAc(3 15 mL). The combined organic layers were washed with brine(3 15 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a residue, which was purified as indicated for each compound (see Supporting material).

References: [1]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 4381 - 4389.

33
[ 69901-85-5 ]
tert-butyl N-[(2R,3S)-3-(4-aminophenyl)-1-(4-methylpiperazin-1-yl)-1-oxobutan-2-yl]carbamate [ No CAS ]
benzyl N-[(S)-({4-[(2S,3R)-3-[(tert-butoxy)carbonyl]amino}-4-(4-methylpiperazin-1-yl)-4-oxobutan-2-yl]phenyl}carbamoyl)(cyclohexyl)methyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; for 18h;	To a solution of 91B (0.125 g, 0.332 mmol, 1.0 eq.) in DMF (1 mL) were added Z-Chg-OH (0.106 g, 0.364 mmol, 1.1 eq.), DIPEA (0.17 mL, 0.996 mmol, 3.0 eq.) and HATU (0.189 g, 0.498 mmol, 1.5 eq.) and the resulting mixture was stirred for 18 h. Aqueous saturated sodium bicarbonate solution was added and then extracted with EtOAc. The combined organic phase was washed with brine, dried over sodium sulfate then concentrated to dryness to afford 92B as an orange solid (0.199 g, 92%) which was used in the next step without further purification. UPLC-MS (basic 2 min): Rt=1.21 min; m/z=650.3 for [M+H]+

References: [1]Patent: US2020/247785,2020,A1 .Location in patent: Paragraph 1319-1320.

34
[ 69901-85-5 ]
methyl (2R)-3-(4-aminophenyl)-2-propanamidopropanoate [ No CAS ]
(R)-methyl 3-(4-((S)-2-(benzyloxycarbonylamino)-2-cyclohexylacetamido)phenyl)-2-propionamidopropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%		To a solution of Z-Chg-OH 4 (0.816 g, 2.80 mmol, 1.2 eq.) in DMF (12.0 mL) was added HATU (1.34 g, 3.51 mmol, 1.5 eq.) and DIPEA (1.22 mL, 7.02 mmol, 3.0 eq) and then stirred at RT for 10 min. A solution of 3 (0.585 g, 2.34 mmol, 1.0 eq,) in DMF (10.0 mL) was added and the resulting mixture was stirred at RT for 1 h. The mixture was concentrated to dryness and the residue triturated with EtOAc/heptane (9:1) to afford 5 as a white solid (1.10 g, 94%). 1H NMR (400 MHz, DMSO-d6) δ 10.01 (s, 1H), 8.78-8.09 (m, 2H), 7.55-7.27 (m, 8H), 7.13 (d, J=8.1 Hz, 2H), 5.03 (s, 2H), 4.43 (td, J=8.6, 5.6 Hz, 1H), 4.00 (t, J=8.3 Hz, 1H), 3.61 (s, 3H), 3.16-3.07 (m, 1H), 2.96 (dd, J=13.8, 5.6 Hz, 1H), 2.83 (dd, J=13.8, 9.2 Hz, 1H), 2.07 (q, J=7.6 Hz, 2H), 1.76-1.51 (m, 4H), 1.17-0.99 (m, 5H), 0.92 (t, J=7.6 Hz, 3H). UPLC-MS (basic 2 min): rt=1.14 min; m/z=541.3 for [M+H]+.

References: [1]Patent: US2020/247785,2020,A1 .Location in patent: Paragraph 0309-0310.

35
[ 69901-85-5 ]
tert-butyl N-[(2R)-3-(4-amino-3-fluorophenyl)-1-(4-methylpiperazin-1-yl)-1-oxopropan-2-yl]carbamate [ No CAS ]
benzyl N-[(S)-({4-[(2R)-2-[(tert-butoxy)carbonyl]amino}-3-(4-methylpiperazin-1-yl)-3-oxopropyl]-2-fluorophenyl}carbamoyl)(cyclohexyl)methyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; for 18h;	To a solution of 43A (1.0 g, 2.63 mmol, 1.0 eq.) in DMF (10 mL) were added Z-Chg-OH (0.919 g, 3.15 mmol, 1.2 eq.), DIPEA (1.8 mL, 10.5 mmol, 4.0 eq.) and HATU (1.50 g, 3.94 mmol, 1.5 eq.) and the resulting mixture was stirred for 18 h. Aqueous saturated sodium bicarbonate solution was added and then extracted with EtOAc. The combined organic phase was washed with brine, dried over sodium sulfate then concentrated to dryness. The residue was purified by flash column chromatography (Silica, 0-10% MeOH, DCM with 5% aq. NH3) to afford 44A as a white solid (1.12 g, 65%). 1H NMR (400 MHz, DMSO-d6) δ 9.71 (s, 1H), 7.71 (t, J=8.3 Hz, 1H), 7.44 (d, J=8.7 Hz, 1H), 7.41-7.23 (m, 4H), 7.23-7.08 (m, 2H), 7.01 (dd, J=8.2, 1.8 Hz, 1H), 5.04 (s, 2H), 4.57 (q, J=8.0 Hz, 1H), 4.18 (t, J=8.0 Hz, 1H), 3.32 (s, 2H), 3.18 (d, J=5.0 Hz, 1H), 2.91-2.64 (m, 2H), 2.23 (s, 3H), 2.13 (s, 4H), 2.01 (d, J=9.8 Hz, 1H), 1.69 (d, J=7.5 Hz, 5H), 1.60 (d, J=10.8 Hz, 1H), 1.31 (s, 9H), 1.09 (d, J=33.8 Hz, 7H). UPLC-MS (basic 4 min): Rt=2.05 min; m/z=654.3 for [M+H]+.

References: [1]Patent: US2020/247785,2020,A1 .Location in patent: Paragraph 1030-1031.

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Code	Phrase
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P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
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P320
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P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
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P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
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P342	If experiencing respiratory symptoms:
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P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
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P378
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P391	Collect spillage. Hazardous to the aquatic environment
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
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H260	In contact with water releases flammable gases which may ignite spontaneously
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Health hazards
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H310	Fatal in contact with skin
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Environmental hazards
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H400	Very toxic to aquatic life
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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

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CAS No.: 69901-85-5

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CAS No.: 69901-85-5

Alternative Products

Product Details of Z-D-Chg-OH

Safety of Z-D-Chg-OH

Application In Synthesis of Z-D-Chg-OH

[ 69901-85-5 ] Synthesis Path-Downstream 1~35

Related Products

Historical Records

Precautionary Statements-General

Prevention

Response

Storage

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