(4S)-Dihydro-4-methyl-2(3H)-furanone → HCID 54557762, compound

HRID 863279Notes

Reaction equation

HRID 863279 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:12][C@@H:13]([CH3:27])[CH2:14][CH2:15][O:16][Si:17]([CH:24]([CH3:26])[CH3:25])([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])[CH:10]=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:28][C@@H:29]1[CH2:34][O:33]C(=O)[CH2:30]1>>[CH2:9]([NH:8][C:34](=[O:33])[C:29](=[CH2:30])[CH2:28][C@H:10]([OH:11])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:12][C@@H:13]([CH3:27])[CH2:14][CH2:15][O:16][Si:17]([CH:18]([CH3:19])[CH3:20])([CH:21]([CH3:23])[CH3:22])[CH:24]([CH3:26])[CH3:25])[CH2:12][CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 11115993(4S)-Dihydro-4-methyl-2(3H)-furanoneHCID 22882392HCID 22882392, compound

Product 1

HCID 54557762HCID 54557762, compound

Procedure

In a manner analogous to that described in Example 72g), the title compound is obtained starting from 3.2 g of 2(S)-tert-butoxycarbonylamino-4(R)-methyl-6-triisopropylsilyloxyhexanal (Rf (D)=0.36), which is prepared by processes analogous to those described in Examples 72h to 72n), starting from (S)-3-methylbutyrolactone, and is purified by FC over 400 g of silica gel (mobile phase gradient from E to B), the two stereoisomers being separated. This gives the title compound (diastereomer I): Rf (A)=0.58; and diastereomer II: Rf (A)=0.47.

Workup

  1. customis obtained
  2. customis prepared by processes analogous to
  3. customis purified by FC over 400 g of silica gel (mobile phase gradient from E to B)
  4. customthe two stereoisomers being separated

Sources & evidence

ORD record
ord-3bdba9218c6a4bd29d3179d1abfa93d4
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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