HCID 11772339, compound → HCID 11279346, compound

HRID 1872450Notes

Reaction equation

HRID 1872450 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:11]2[C@H:7]1[CH2:8][C@@H:9]([OH:25])[C@@:10]2([N:22]=[N+:23]=[N-:24])[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].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[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+:23]=[N-:24])[C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 11772339HCID 11772339, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 11279346HCID 11279346, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1S,2R,3R,5R,6S)-2-Azido-3-hydroxy-bicyclo [3.1.0] hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (VII-1) (960 mg, 2.78 mmol) in DCM (18 mL) was added PCC (2.40 g, 50% on silica gel) at 0° C. and stirring was continued at 23° C. for 20 h. The reaction mixture was placed on a silica gel column and the product was eluted with DCM to yield (1S,2R,5R,6S)-2-azido-3-oxo- bicyclo[3.1.0]hexane-2,6-dicarboxylic acid 2-benzyl ester 6-ethyl ester (IX-1) (746 mg, 78%) as a white solid. 1H-NMR (250 MHz, CDCl3) □1.27 (3H, t, J=7.2 Hz), 1.62 (1H, t,J=3.4 Hz), 2.29 (1H, m), 2.44 (1H, dd,J=7.7, 3.1 Hz), 2.55 (1H, d, J=19.2 Hz), 2.98 (1H, dd, J=19.2, 5.6 Hz), 4.13 (2H, q, J=7.2 Hz), 5.29 (2H, s), 7.36-7.40 (5H, m); MS[ISP]361 (M+NH4+); mp 46-48° C.; □D20 +210.910 (c=1.07, CHCl3).

Workup

  1. washthe product was eluted with DCM

Sources & evidence

ORD record
ord-79db8c65bf7c4c899ff23cd9f25212f9
Source dataset
uspto-grants-2000_08
Patent number
US06107342

Reaction notes

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