Benzyl chloroformate → HCID 70048501, compound

HRID 1780258Notes

Reaction equation

Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][CH:6]([O:9][CH2:10][C:11]([NH:13][C@H:14]([C:19]([NH:21][C@@H:22]([CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C@H:23]([OH:38])[C:24]([N:26]2[CH2:37][CH2:36][CH2:35][C@H:27]2[C:28]([NH:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:25])=[O:20])[CH2:15][C:16](=[O:18])[NH2:17])=[O:12])[CH2:5][CH2:4]1.[CH2:46]([O:53][C:54](Cl)=[O:55])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>>[CH2:46]([O:53][C:54]([NH:2][CH:3]1[CH2:8][CH2:7][CH:6]([O:9][CH2:10][C:11]([NH:13][C@H:14]([C:19]([NH:21][C@@H:22]([CH2:39][C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C@H:23]([OH:38])[C:24]([N:26]2[CH2:37][CH2:36][CH2:35][C@H:27]2[C:28]([NH:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:25])=[O:20])[CH2:15][C:16](=[O:18])[NH2:17])=[O:12])[CH2:5][CH2:4]1)=[O:55])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

Reactant 2

HCID 10387Benzyl chloroformate

HCID 86750828HCID 86750828, compound

Product 1

HCID 70048501HCID 70048501, compoundYield 47.9%

Procedure

Following a procedure similar to that described in Example 30, but using 40 mg (61.2 μmol) of 1-{(2S,3S)-3-[N2 -(4-aminocyclohexyloxy)acetyl-L-asparaginyl]amino-2-hydroxy-4-phenylbutyryl}-N-t-butyl-L-prolinamide hydrochloride (prepared as described in Example 58) and 0.01 ml (67.3 μmol) of benzyloxycarbonyl chloride, 22 mg of the title compound were obtained as a colorless powder, melting at 109°-114° C.

Sources & evidence

ORD record: ord-9d117f8da21046919565a173b045edaa
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05629406

Reaction notes

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