HCID 70459262, compound → HCID 178475058, compound

HRID 2413712Notes

Reaction equation

HRID 2413712 reaction equation
[C:1]([NH:4][C@H:5]1[C:8](=[O:9])[NH:7][C@H:6]1[C:10]([OH:12])=[O:11])(=[O:3])[CH3:2].[NH2:13][C@H:14]([C:21]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([NH2:27])=[O:26])=[O:22])[CH2:15][C:16]1[N:20]=[CH:19][NH:18][CH:17]=1>>[C:1]([NH:4][C@@H:5]1[C:8](=[O:9])[NH:7][C@@H:6]1[C:10]([NH:13][C@H:14]([C:21]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([NH2:27])=[O:26])=[O:22])[CH2:15][C:16]1[N:20]=[CH:19][NH:18][CH:17]=1)=[O:12])(=[O:3])[CH3:2].[C:1]([NH:4][C@H:5]1[C:8](=[O:9])[NH:7][C@H:6]1[C:10]([NH:13][C@H:14]([C:21]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([NH2:27])=[O:26])=[O:22])[CH2:15][C:16]1[N:20]=[CH:19][NH:18][CH:17]=1)=[O:11])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 70459262HCID 70459262, compoundHCID 178513962HCID 178513962, compound

Product 2

HCID 178475058HCID 178475058, compoundHCID 178475059HCID 178475059, compound

Procedure

The residue containing compound (32) obtained in Reference Example 7 was reacted with L-histidyl-L-prolinamide (free base) in a similar manner as above. The thus obtained reaction mixture was purified by column chromatography using silica gel (150 g). The desired compound was eluted with ethyl acetate-methanol-ammonia water (20:10:1). After the solvent was removed, the product was lyophilized. Thus, 274 mg was obtained as a mixture of Nα -[(2S,3S)-3-acetylamino-4-oxo-2-azetidinylcarbonyl]-L-histidyl-L-prolinamide (34a) and Nα -[(2R,3R)-3-acetylamino-4-oxo-2-azetidinylcarbonyl]-L-histidyl-L-prolinamide (34b).

Workup

  1. customobtained in Reference Example 7
  2. customThe thus obtained reaction mixture
  3. customwas purified by column chromatography
  4. washThe desired compound was eluted with ethyl acetate-methanol-ammonia water (20:10:1)
  5. customAfter the solvent was removed

Sources & evidence

ORD record
ord-910c2426c29a4bd8bb9ba7f29c116ec2
Source dataset
uspto-grants-1988_01
Patent number
US04719207

Reaction notes

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