HCID 17773803, compound → HCID 20639574, compound

HRID 568278Notes

Reaction equation

HRID 568278 reaction equation
[CH3:1][C:2]1[N:9]2[C:5]([S:6][CH:7]=[CH:8]2)=[CH:4][N:3]=1.[CH2:10]([O:13][C:14]([N:16]1[C@H:20]([CH:21]=[O:22])[CH2:19][C@@H:18]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[CH2:17]1)=[O:15])[CH:11]=[CH2:12]>>[CH2:10]([O:13][C:14]([N:16]1[C@H:20]([CH:21]([OH:22])[C:7]2[S:6][C:5]3=[CH:4][N:3]=[C:2]([CH3:1])[N:9]3[CH:8]=2)[CH2:19][C@@H:18]([O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:25])[CH3:26])[CH2:17]1)=[O:15])[CH:11]=[CH2:12]

Participants

3

Reactant 2

HCID 17773803HCID 17773803, compoundHCID 22870383(2S,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-formylpyrrolidine

Product 1

HCID 20639574HCID 20639574, compoundYield 18.5%

Procedure

The procedure of Synthesis Example 10-a) is repeated, except that 1.53 g of 5-methylimidazo[5,1-b]thiazole and 3.46 g of (3R,5S)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-formylpyrrolidine is used and the purification is successively performed by column chromatography on silica gel (ethyl acetate:methanol=9:1) and on Sephadex LH-20 (dichloromethane:methanol=1:1) to give 0.92 g of (3R,5S)-1-allyloxycarbonyl-3-t-butyldimethylsilyloxy-5-[1-hydroxy-1-(5-methylimidazo[5,1-b]thiazol-2-yl)methyl]pyrrolidine (a diastereomer mixture) as a slightly yellow amorphous material.

Workup

  1. customThe procedure of Synthesis Example 10-a)
  2. customthe purification

Sources & evidence

ORD record
ord-12da771ab59e405a90a6d91598e5790c
Source dataset
uspto-grants-2001_01
Patent number
US06180622B2

Reaction notes

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