Methyl chloroformate → HCID 178457312, compound

HRID 1920132Notes

Reaction equation

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

Participants

Reactant 2

HCID 6586Methyl chloroformate

HCID 178457311HCID 178457311, compound

Product 1

HCID 178457312HCID 178457312, compoundYield 97.2%

Procedure

The same operation as in Example 13 was performed, except for using the compound (200 mg) obtained in Example 16 and methyl chloroformate (54 mg), and then the obtained crude product was purified by silica gel chromatography (ethyl acetate:10%-saturated aqueous ammonia-methanol=1:0→85:15) to obtain the title compound (210 mg) having the following physical properties.

Workup

customthe obtained crude product
customwas purified by silica gel chromatography (ethyl acetate:10%-saturated aqueous ammonia-methanol=1:0→85:15)

Sources & evidence

ORD record: ord-a94dc2db899a4fe78a157d72d14cd77a
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168783B2

Reaction notes

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