N-(9-fluorenylcarbonyl)glycine → 2-[[[N-(9-fluorenylcarbonyl)glycyl]-L-valyl]amino]-6-methylbenzoic acid

HRID 1729249Notes

Reaction equation

HRID 1729249 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([NH:11][C:12](=[O:18])[C@H:13]([CH:15]([CH3:17])[CH3:16])[NH2:14])[CH:5]=[CH:4][CH:3]=1.[CH:19]1[C:31]2[CH:30]([C:32]([NH:34][CH2:35][C:36](O)=[O:37])=[O:33])[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]=2[CH:22]=[CH:21][CH:20]=1>>[CH:28]1[C:29]2[CH:30]([C:32]([NH:34][CH2:35][C:36]([NH:14][C@H:13]([C:12]([NH:11][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[C:7]=3[C:8]([OH:10])=[O:9])=[O:18])[CH:15]([CH3:16])[CH3:17])=[O:37])=[O:33])[C:31]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:24]=2[CH:25]=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 19011682N-(9-fluorenylcarbonyl)glycineHCID 541805686-methyl-2-(L-valylamino)benzoic acid

Product 1

HCID 541955892-[[[N-(9-fluorenylcarbonyl)glycyl]-L-valyl]amino]-6-methylbenzoic acidYield 33.4%

Procedure

84 mg of 2-[[[N-(9-fluorenylcarbonyl)glycyl]-L-valyl]amino]-6-methylbenzoic acid was prepared exactly as in step c) of Example 3, except that 126 mg of 6-methyl-2-(L-valylamino)benzoic acid was subjected to a condensation reaction with 188 mg of N-(9-fluorenylcarbonyl)glycine in place of 9-fluorenyloxyacetic acid used in Example 3.

Sources & evidence

ORD record
ord-af4727b6c65a443582c7c6452f348e17
Source dataset
uspto-grants-1994_07
Patent number
US05332734

Reaction notes

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