4-Nitrophenyl chloroformate → HCID 70059124, compound

HRID 1780254Notes

Reaction equation

Cl.[CH3:2][NH:3][C:4]1[CH:46]=[CH:45][C:7]([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])=[CH:6][CH:5]=1.[N+:47]([C:50]1[CH:59]=[CH:58][C:53]([O:54][C:55](Cl)=[O:56])=[CH:52][CH:51]=1)([O-:49])=[O:48]>>[N+:47]([C:50]1[CH:59]=[CH:58][C:53]([O:54][C:55]([N:3]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]([NH:12][C@H:13]([C:18]([NH:20][C@@H:21]([CH2:38][C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[C@H:22]([OH:37])[C:23]([N:25]3[CH2:36][CH2:35][CH2:34][C@H:26]3[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])=[CH:45][CH:46]=2)[CH3:2])=[O:56])=[CH:52][CH:51]=1)([O-:49])=[O:48]

Participants

Reactant 2

HCID 821294-Nitrophenyl chloroformate

HCID 70050717HCID 70050717, compound

Product 1

HCID 70059124HCID 70059124, compoundYield 20.2%

Procedure

Following a procedure similar to that described in Example 30, but using 500 mg (0.76 mmol) of 1-{(2S,3S)-3-[N2 -(p-methylaminophenoxy)acetyl-L-asparaginyl]amino-2-hydroxy-4-phenylbutyryl}-N-t-butyl-L-prolinamide hydrochloride (prepared as described in Example 20) and 236 mg (1.13 mmol) of 4-nitrophenoxycarbonyl chloride, 121 mg of the title compound were obtained as a colorless powder, melting at 116°-119° C.

Sources & evidence

ORD record: ord-32429a784ae74c37a3bff30555dcc1d7
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05629406

Reaction notes

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