(2R)-Oxiran-2-ylmethyl butanoate → HCID 67273729, compound

HRID 1163346Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([N:15]([C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:35])[C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23]([O:25][CH2:26][C:27]3C=CC=CC=3)=[O:24])=[CH:18][C:17]=2[F:33])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].CC([N-]C(C)C)C.[C:52](OC[C@@H]1OC1)(=[O:56])CCC>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH:13]([N:15]([C:34]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:35])[C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][C@H:26]([CH2:52][OH:56])[O:25][C:23]3=[O:24])=[CH:18][C:17]=2[F:33])[CH2:14]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 0.916 g of 3-(benzyloxycarbonyl-(4-benzyloxycarbonylamino-2-fluoro-phenyl)-amino]-azetidine-1-carboxylic acid benzyl ester (1.56 mmol) in 5 ml THF were added at −15° C. 0.767 ml of a 2.25M LDA (1.7 mmol) solution in THF. The mixture was allowed to warm up to 0° C. and stirred for 5 min. Then, 0.26 ml of (R)-glycidyl butyrate (1.87 mmol) was added and the yellow solution was stirred for 2 h at RT. The reaction was quenched with a saturated solution of ammonium chloride. The mixture was diluted with ethyl acetate, the org. layer washed with water and brine and dried over Mg sulfate. The residue was purified by chromatography using a 95/5 dichloromethane/methanol mixture as eluent.

Workup

stirringthe yellow solution was stirred for 2 h at RT
customThe reaction was quenched with a saturated solution of ammonium chloride
additionThe mixture was diluted with ethyl acetate
washlayer washed with water and brine
dry with materialdried over Mg sulfate
customThe residue was purified by chromatography

Sources & evidence

ORD record: ord-d9db0578e0f64e03b7cce3a50377d082
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820823B2

Reaction notes

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