Acetic Acid → HCID 86618210, compound

HRID 1669519Notes

Reaction equation

C[O:2][C:3](=O)[C@@H:4]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1.[H-].C([Al+]CC(C)C)C(C)C.CC(O)=O>C1(C)C=CC=CC=1>[C:24]([O:23][C:21](=[O:22])[NH:20][C@H:4]([CH:3]=[O:2])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[CH:8][CH:7]=1)([CH3:25])([CH3:27])[CH3:26]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of (S)-2-tert-Butoxycarbonylamino-3-[4-(4-chloro-phenoxy)-phenyl]-propionic acid methyl ester (107 mg, 0.26 mmol, 1 eq.) in toluene (5 ml) was added dropwise diisobutylaluminium hydride (1 M in hexane, 0.6 ml, 2.3 eq.) by a syringe with stirring under Ar at −78° C. After the addition was complete, the mixture was stirred at the same temperature for 2 hr and then AcOH (0.2 ml) was added. The mixture was allowed to warm to room temperature overnight. The mixture was partitioned between water and ethyl acetate. EA layer was separated and aqueous layer was extracted with EA. The combined EA layers were dried over anhydrous MgSO4. After the volatile material was removed, the desired product was obtained (68 mg, 70% yield). The product thus obtained was forward to the next step without any further purification.

Workup

additionAfter the addition
stirringthe mixture was stirred at the same temperature for 2 hr
temperatureto warm to room temperature overnight
customThe mixture was partitioned between water and ethyl acetate
customEA layer was separated
extractionaqueous layer was extracted with EA
dry with materialThe combined EA layers were dried over anhydrous MgSO4
customAfter the volatile material was removed

Sources & evidence

ORD record: ord-d7668114de48405cb993a7af9f092148
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989480B2

Reaction notes

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