Isopropanol → HCID 59922341, compound

HRID 278943Notes

Reaction equation

HRID 278943 reaction equation
[OH:1][NH:2][C:3](=[O:24])[C:4]([OH:23])([CH3:22])[CH2:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)(=[O:8])=[O:7].C(O)(C)C>C(O)C>[OH:1][NH:2][C:3](=[O:24])[C@@:4]([OH:23])([CH3:22])[CH2:5][S:6]([C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:13][CH:14]=1)(=[O:7])=[O:8]

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 22732201HCID 22732201, compound

Product 1

HCID 59922341HCID 59922341, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N,2-dihydroxy-2-methyl-3-[(4-phenoxyphenyl)sulfonyl)propanamide (20 g) in ethanol (1500 mL) was sequentially injected in 12 mL portions onto a Prochrom® column (50 mm I.D., 36 mm bed length) packed with Chiralpak® AD. The mobile phase used was 30% isopropyl alcohol/70% heptane. Fractions were collected automatically and pooled. The first eluting peak was collected and the appropriate fractions were combined to provide the title compound (8.351 g). HPLC purity: 100%.

Workup

  1. customFractions were collected automatically
  2. customThe first eluting peak was collected

Sources & evidence

ORD record
ord-9ac5c91bfe924048b9134ce50f91355d
Source dataset
uspto-grants-2002_03
Patent number
US06362183B1

Reaction notes

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