Water → HCID 86757986, compound

HRID 843726Notes

Reaction equation

Cl.[CH2:2]([O:4][C:5](=[O:28])[C@@H:6]([NH2:27])[CH2:7][NH:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:12]1)=[O:10])[CH3:3].C(N(CC)CC)C.[C:36](Cl)(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.O>ClCCl>[CH2:2]([O:4][C:5](=[O:28])[C@@H:6]([NH:27][C:36](=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH2:7][NH:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH2:14][N:13]([C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])[CH2:12]1)=[O:10])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of N-[(R)-(1-benzyloxycarbonyl-3-piperidyl)carbonyl]-2(S)-amino-β-alanine ethyl ester hydrochloride (300 mg) in dichloromethane (3 ml) was added triethylamine (222 μl) and benzoyl chloride (93 μl) under stirring at 0° C. After stirring at ambient temperature for 1 hour, the mixture was poured into water and extracted with dichloromethane. The extract was washed with water, saturated aqueous NaHCO3 solution, water and brine, and dried over MgSO4, and evaporated in vacuo. The residue was recrystallized from diethyl ether to give N-[(R)-(1-benzyloxycarbonyl-3-piperidyl)carbonyl]-2(S)-benzoylamino-β-alanine ethyl ester (349 mg).

Workup

stirringAfter stirring at ambient temperature for 1 hour
extractionextracted with dichloromethane
washThe extract was washed with water, saturated aqueous NaHCO3 solution, water and brine
dry with materialdried over MgSO4
customevaporated in vacuo
customThe residue was recrystallized from diethyl ether

Sources & evidence

ORD record: ord-f510756482054f55b68cae557fba3f44
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06380215B1

Reaction notes

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