HCID 86757661, compound → HCID 9806530, compound

HRID 2269355Notes

Reaction equation

[CH3:1][C:2]([CH3:42])([CH3:41])[C@H:3]([NH:12][C:13](=[O:40])[C@H:14]([CH2:27][CH:28]1[CH2:33][CH2:32][CH:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:30][CH2:29]1)[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>[CH3:41][C:2]([CH3:1])([CH3:42])[C@H:3]([NH:12][C:13](=[O:40])[C@H:14]([CH2:27][CH:28]1[CH2:29][CH2:30][CH:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:32][CH2:33]1)[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

Conditions

Temperature: 40 °C

Procedure

A mixture of (2R,3S)-3-(formyl-tetrahydropyranyloxyamino)-2-(4-phenylcyclohexylmethyl)butanoic acid [(1S)-2,2-dimethyl-1-(1,3-thiazol-2-ylcarbamoyl)-1-propyl]amide (0.12 g, 0.20 mmol) in 80% acetic acid (10 mL) is heated at 40° C. for 18 h. The mixture is concentrated in vauco, the residue is taken up in ethanol and concentrated in vacuo. Repeating the ethanol treatment several times and addition of water is followed by stirring at 25° C. for 18 h. The resulting solid is filtered, washed with water, and dried to give 0.083 g (80%) of (2R,3S)-3-(formyl-hydroxyamino)-2-(4-phenylcyclohexylmethyl)butanoic acid [(1S)-2,2-dimethyl-1-(1,3-thiazol-2-ylcarbamoyl)-1-propyl]amide as a white solid, m.p. 213-214° C.

Workup

concentrationThe mixture is concentrated in vauco
concentrationconcentrated in vacuo
additionthe ethanol treatment several times and addition of water
filtrationThe resulting solid is filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-44fd4120bf5249edb57e1efc3e220aae
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329400B1

Reaction notes

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