Potassium Carbonate → 4-Methoxybenzyl (2RS)-2-hydroxy-2-[(3R,4R)-3-phenyl-acetamido-4-[(RS)-tetrahydrofuran-2-yl-carbonylmethylthio]-azetidin-2-on-1-yl]acetate

HRID 612284Notes

Reaction equation

HRID 612284 reaction equation
[OH:1][CH:2]([N:15]1[C@H:18]([SH:19])[C@H:17]([NH:20][C:21](=[O:29])[CH2:22]C2C=CC=CC=2)[C:16]1=[O:30])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:4].Br[CH2:32][C:33]([CH:35]1[CH2:39][CH2:38][CH2:37][O:36]1)=[O:34].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)(=O)C>[OH:1][CH:2]([N:15]1[C@H:18]([S:19][CH2:32][C:33]([CH:35]2[CH2:39][CH2:38][CH2:37][O:36]2)=[O:34])[C@@:17]([NH:20][C:21](=[O:29])[CH3:22])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:16]1=[O:30])[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 219089652-Bromo-1-(oxolan-2-yl)ethan-1-oneHCID 544549564-methoxybenzyl (2RS)-2-hydroxy-2-[(3R,4R)-4-mercapto-3-phenylacetamidoazetidin-2-on-1-yl]acetate

Product 1

HCID 1317214994-Methoxybenzyl (2RS)-2-hydroxy-2-[(3R,4R)-3-phenyl-acetamido-4-[(RS)-tetrahydrofuran-2-yl-carbonylmethylthio]-azetidin-2-on-1-yl]acetate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

The crude thiol was dissolved in acetone (35 ml) and treated with a solution of (RS)-2-bromoacetyltetrahydrofuran (3.48 g, 18.0 mmol) in acetone (5 ml). After 10 min, potassium carbonate (1.24 g, 8.9 mmol) was added, and the mixture stirred for a further 30min. The reaction mixture was diluted with ethyl acetate, washed successively with water (x2) and brine, dried and concentrated. The residue was flash chromatographed on silica gel eluting with 50, 70 and 80% ethyl acetate in hexane yielding the title compound as a colourless foam (5.40 g, 55%); νmax (CH2Cl2) 3409, 1781, 1745, 1684, 1613, 1516 cm-1. [Mass spectrum +ve ion (3-nitrobenzyl alcohol, sodium acetate) MNa+ (565)].

Workup

  1. washwashed successively with water (x2) and brine
  2. customdried
  3. concentrationconcentrated
  4. customchromatographed on silica gel eluting with 50, 70 and 80% ethyl acetate in hexane yielding the title compound as a colourless foam (5.40 g, 55%)

Sources & evidence

ORD record
ord-53b9146ca141459c89dfdcf2c80bea05
Source dataset
uspto-grants-1999_12
Patent number
US06001997

Reaction notes

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