HCID 11279346, compound → HCID 86755666, compound

HRID 1872455Notes

Reaction equation

HRID 1872455 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:11]2[C@H:7]1[CH2:8][C:9](=[O:25])[C@@:10]2([N:22]=[N+]=[N-])[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:5])[CH3:2].[C:26]([OH:29])(=S)[CH3:27]>>[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:11]2[C@H:7]1[CH2:8][C:9](=[O:25])[C@@:10]2([NH:22][C:26](=[O:29])[CH3:27])[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 11279346HCID 11279346, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86755666HCID 86755666, compoundYield 71%

Procedure

A solution of (1S,2R,5R,6S)-2-Azido-3-oxo-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (IX) (974 mg, 2.84 mmol) in thioacetic acid (6.5 mL) was stirred at 70° C. for 2 d. The reaction mixture was concentrated in vacuum and subjected to silica gel column chromatography with hexane/ethyl acetate 3:2->1:1 to yield (1S,2R,5R,6S)-2-acetylamino-3-oxo-bicyclo [3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (XVI) (726 mg, 71%) as a pink oil. 1H-NMR (250 MHz, CDCl3) □1.25 (3H, t, 1=7.1 Hz), 1.63 (1H, t, J=3.5 Hz), 2.05 (3H, s), 2.32 (1H, ddd,J=7, 6,3.5 Hz), 2.54 (1H, d,J=19 Hz), 2.90 (1H, dd,J=19, 6 Hz), 3.06 (1H, dd, J=7, 3.5 Hz), 4.12 (2H, m), 5.16 (1H, d, J=12 Hz), 5.25 (1H, d, J=12 Hz), 7.24-7.35 (5H, m); MS[ISP] 360 (M+H+); □D20 +44.33° (c=0.97, CHCl3).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuum

Sources & evidence

ORD record
ord-db6d69e261fa44038c102633575b372d
Source dataset
uspto-grants-2000_08
Patent number
US06107342

Reaction notes

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