HCID 86756437, compound → HCID 86756436, compound

HRID 636017Notes

Reaction equation

[N+:1]([N:4]=[N:5][CH2:6][NH:7][CH2:8][CH2:9][CH2:10][C@H:11]([NH:20][C:21](=[O:44])[C@H:22]([CH2:37][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1)[C@@H:23]([N:27]([CH:35]=[O:36])[O:28]C1CCCCO1)[CH2:24][CH2:25][CH3:26])[C:12](=[O:19])[NH:13][C:14]1[S:15][CH:16]=[CH:17][N:18]=1)([O-:3])=[O:2]>C(O)(=O)C>[N+:1]([N:4]=[N:5][CH2:6][NH:7][CH2:8][CH2:9][CH2:10][C@H:11]([NH:20][C:21](=[O:44])[C@H:22]([CH2:37][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1)[C@@H:23]([N:27]([CH:35]=[O:36])[OH:28])[CH2:24][CH2:25][CH3:26])[C:12](=[O:19])[NH:13][C:14]1[S:15][CH:16]=[CH:17][N:18]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 40 °C

Procedure

(2R,3S)-3-(Formyl-2-tetrahydropyranyloxyamino)-2-(cyclohexylmethyl)hexanoic acid [(1S)-4-(nitroimino-amino)methylamino-1-(1,3-thiazol-2-ylcarbamoyl)-1-butyl]amide (115 mg, 0.180 mmol) is dissolved in 2 mL of 80% acetic acid and heated at 40° C. for 20 h. Concentration in vacuo and trituration with dichloromethane—ether provided 81 mg of (2R,3S)-3-(formyl-hydroxyamino)-2-(cyclohexylmethyl)hexanoic acid [(1S)-4-(nitroimino-amino)methylamino-1-(1,3-thiazol-2-ylcarbamoyl)-1-butyl]amide as a solid.

Workup

concentrationConcentration in vacuo and trituration with dichloromethane—ether

Sources & evidence

ORD record: ord-23952add59564b46828b93755c81351a
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06191150B1

Reaction notes

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