Acetic Acid → HCID 57014607, compound

HRID 325983Notes

Reaction equation

HRID 325983 reaction equation
[S:1]([O:11][CH2:12][C:13]1([CH2:35][O:36][S:37]([C:40]2[CH:46]=[CH:45][C:43]([CH3:44])=[CH:42][CH:41]=2)(=[O:39])=[O:38])[CH2:26][C@@H:25]2[C@:16]34[CH2:29][CH2:28][N:27]([CH3:30])[C@@H:24]2[CH2:23][C:22]2[CH:21]=[CH:20][C:19]([O:31][CH3:32])=[C:18]([O:33][C@H:15]3[C:14]1=[O:34])[C:17]4=2)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[BH4-].[Na+].CC(O)=O>CCO.C(Cl)(Cl)Cl>[S:37]([O:36][CH2:35][C:13]1([CH2:12][O:11][S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:2])=[O:3])[CH2:26][C@@H:25]2[C@:16]34[CH2:29][CH2:28][N:27]([CH3:30])[C@@H:24]2[CH2:23][C:22]2[CH:21]=[CH:20][C:19]([O:31][CH3:32])=[C:18]([O:33][C@H:15]3[C@H:14]1[OH:34])[C:17]4=2)([C:40]1[CH:41]=[CH:42][C:43]([CH3:44])=[CH:45][CH:46]=1)(=[O:39])=[O:38]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 86739365HCID 86739365, compound

Product 1

HCID 57014607HCID 57014607, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of 10 (20.0 g, 30 mmole) in a mixture of 95% EtOH (200 mL) and CHCl3 (100 mL) was cooled in an ice bath and NaBH4 (3.4 g, 90 mmole) added portionwise over 10 min. The mixture was stirred for 90 min. in the cold, excess HOAc added to destroy the hydride and the solution evaporated. The residue was partitioned between CHCl3 and dilute NH4OH and further processed in the usual fashion. Evaporation gave a quantitative yield of 11 as a foam which contained traces of 6β-ol 2 and other impurities; NMR δ 4.41 (d, 1H, H5, J=5.5 Hz). This material was converted to 12 without further purification.

Workup

  1. temperaturewas cooled in an ice bath
  2. additionadded
  3. customto destroy the hydride
  4. customthe solution evaporated
  5. customThe residue was partitioned between CHCl3 and dilute NH4OH
  6. customEvaporation

Sources & evidence

ORD record
ord-22e150253041488fadc33358e7c7160e
Source dataset
uspto-grants-1984_04
Patent number
US04443605

Reaction notes

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