Sodium borohydride → HCID 54462572, compound

HRID 375753Notes

Reaction equation

HRID 375753 reaction equation
[BH4-].[Na+].[Si:3]([O:10][C:11]1[CH:12]=[C:13]([O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])[C:14]2[CH2:25][S:24][CH2:23][C@@H:22]([C:26](OC)=[O:27])[NH:21][C:20](=[O:30])[C@@H:19]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:18][O:17][C:16](=[O:39])[C:15]=2[C:40]=1[CH3:41])([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4]>CO.CO.O1CCCC1>[Si:3]([O:10][C:11]1[CH:12]=[C:13]([O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:44])[CH3:45])[C:14]2[CH2:25][S:24][CH2:23][C@@H:22]([CH2:26][OH:27])[NH:21][C:20](=[O:30])[C@@H:19]([NH:31][C:32]([O:34][C:35]([CH3:36])([CH3:37])[CH3:38])=[O:33])[CH2:18][O:17][C:16](=[O:39])[C:15]=2[C:40]=1[CH3:41])([C:6]([CH3:9])([CH3:7])[CH3:8])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 10996150HCID 10996150, compound

Product 1

HCID 54462572HCID 54462572, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 114 mg of sodium borohydride in 1.5 ml of 80% aqueous methanol, cooled to 0° C., was added within 5 minutes a solution of 214 mg of tert-butyl (4R, 7S)-12,14-bis(tert-butyldimethylsilyloxy)-1,3,4,5,6,7,8,10-octahydro-4-(methoxycarbonyl)-11-methyl-6,10-dioxo-9,2,5-benzoxathiaazacyclododecine-7-carbamate in 1.5 ml of methanol/tetrahydro-furan (1:1, v/v). The solution was stirred at 0° C. for 30 minutes, and then poured into ice-cold 0.5N hydrochloric acid. The mixture was extracted with ethyl acetate, and the organic layer was washed with brine, and dried over sodium sulfate. The solvent was evaporated in vacuo to yield 181 mg of tert-butyl (4R, 7S)-12, 14-bis (tert-butyldimethylsilyloxy)-1,3,4,5,6,7,8, 10-octahydro-4-hydroxymethyl-11-methyl-6,10-dioxo-9,2,5-benzoxathiaazacyclododecine-7-carbamate as an amorphous solid. This material was treated with ammonium fluoride in methanol in an analogous manner to the procedure described in Example 13 to yield, after crystallization from ethyl acetate/methanol/hexane, tert-butyl (4R, 7S)-1,3,4,5,6,7,8,10 -octahydro-12,14-dihydroxy-4-hydroxymethyl-11-methyl-6,10-dioxo-9,2,5-benzoxathiaazacyclododecine-7-carbamate as a white solid.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-9233f3584bda431fa45ad89fa75b00e6
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

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