Benzyl chloroformate → HCID 86750825, compound

HRID 1780257Notes

Reaction equation

Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([O:8][CH2:9][C:10]([NH:12][C@H:13]([C:18]([NH:20][C@@H:21]([CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C@H:22]([OH:37])[C:23]([N:25]2[CH2:36][CH2:35][CH2:34][C@H:26]2[C:27]([NH:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:24])=[O:19])[CH2:14][C:15](=[O:17])[NH2:16])=[O:11])[CH2:4][CH2:3]1.[CH2:45]([O:52][C:53](Cl)=[O:54])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>>[CH2:45]([O:52][C:53]([N:2]1[CH2:7][CH2:6][CH:5]([O:8][CH2:9][C:10]([NH:12][C@H:13]([C:18]([NH:20][C@@H:21]([CH2:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[C@H:22]([OH:37])[C:23]([N:25]2[CH2:36][CH2:35][CH2:34][C@H:26]2[C:27]([NH:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])=[O:24])=[O:19])[CH2:14][C:15](=[O:17])[NH2:16])=[O:11])[CH2:4][CH2:3]1)=[O:54])[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

Reactant 2

HCID 10387Benzyl chloroformate

HCID 86750826HCID 86750826, compound

Product 1

HCID 86750825HCID 86750825, compoundYield 78.6%

Procedure

Following a procedure similar to that described in Example 30, but using 120 mg (0.19 mmol) of 1-{(2S,3S)-3-[N2 -(4-piperidyloxy)acetyl-L-asparaginyl]amino-2-hydroxy-4-phenylbutyryl}-N-t-butyl-L-prolinamide hydrochloride (prepared as described in Example 56) and 0.03 ml (0.21 mmol) of benzyloxycarbonyl chloride, 110 mg of the title compound were obtained as a colorless powder, melting at 98°-104° C.

Sources & evidence

ORD record: ord-55ab241bd3e8423c8e21d3bbfcf4a50f
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05629406

Reaction notes

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