HCID 86756443, compound → HCID 86756444, compound

HRID 636028Notes

Reaction equation

HRID 636028 reaction equation
[CH3:1][C@H:2]([CH2:32][CH2:33][NH:34][CH2:35][N:36]=[N:37][N+:38]([O-:40])=[O:39])[C@H:3]([NH:12][C:13](=[O:31])[C@H:14]([CH2:27][CH:28]([CH3:30])[CH3:29])[C@@H:15]([N:17]([CH:25]=[O:26])[O:18]C1CCCCO1)[CH3:16])[C:4](=[O:11])[NH:5][C:6]1[S:7][CH:8]=[CH:9][N:10]=1>C(O)(=O)C>[CH3:1][C@H:2]([CH2:32][CH2:33][NH:34][CH2:35][N:36]=[N:37][N+:38]([O-:40])=[O:39])[C@H:3]([NH:12][C:13](=[O:31])[C@H:14]([CH2:27][CH:28]([CH3:29])[CH3:30])[C@@H:15]([N:17]([CH:25]=[O:26])[OH:18])[CH3:16])[C:4](=[O:11])[NH:5][C:6]1[S:7][CH:8]=[CH:9][N:10]=1

Participants

3

Reactant 1

HCID 86756443HCID 86756443, compound

Product 1

HCID 86756444HCID 86756444, compoundYield 106%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

(2R,3S)-3-(Formyl-tetrahydropyranyloxyamino)-2-(2-methyl-1-propyl)butanoic acid [(1S,2R)-2-methyl-4-(nitroimino-amino)methylamino-1-(1,3-thiazol-2-ylcarbamoyl)-1-butyl]amide (30 mg, 0.049 mmol) is dissolved in 2 mL of 80% acetic acid and heated at 40° C. for 20 h. Concentration in vacuo, trituration with dichloromethane/ether, and collection of the product provides 26 mg of (2R,3S)-3-(formyl-hydroxyamino)-2-(2-methyl-1-propyl)butanoic acid [(1S,2R)-2-methyl-4-(nitroimino-amino)methylamino-1-(1,3-thiazol-2-ylcarbamoyl)-1-butyl]amide as a solid.

Workup

  1. concentrationConcentration in vacuo, trituration
  2. customwith dichloromethane/ether, and collection of the product

Sources & evidence

ORD record
ord-3377746b415f4471bfcdf0ee915235d6
Source dataset
uspto-grants-2001_02
Patent number
US06191150B1

Reaction notes

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