Sodium borohydride → HCID 70161399, compound

HRID 1251092Notes

Reaction equation

HRID 1251092 reaction equation
[BH4-].[Na+].[F:3][C:4]1([F:46])[CH2:5][CH2:6][N:7]([C:32]([C:34]2[S:38][C:37]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[N:36][C:35]=2[CH3:45])=[O:33])[C:8]2[CH:31]=[CH:30][CH:29]=[CH:28][C:9]=2/[C:10]/1=[CH:11]/[C:12]([N:14]1[CH2:19][CH2:18][CH:17]([C:20](=[O:27])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:16][CH2:15]1)=[O:13]>O1CCCC1CCO.C(OCC)(=O)C>[F:46][C:4]1([F:3])[CH2:5][CH2:6][N:7]([C:32]([C:34]2[S:38][C:37]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[N:36][C:35]=2[CH3:45])=[O:33])[C:8]2[CH:31]=[CH:30][CH:29]=[CH:28][C:9]=2/[C:10]/1=[CH:11]/[C:12]([N:14]1[CH2:15][CH2:16][CH:17]([CH:20]([OH:27])[CH2:21][CH2:22][OH:23])[CH2:18][CH2:19]1)=[O:13].[F:46][C:4]1([F:3])[CH2:5][CH2:6][N:7]([C:32]([C:34]2[S:38][C:37]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[N:36][C:35]=2[CH3:45])=[O:33])[C:8]2[CH:31]=[CH:30][CH:29]=[CH:28][C:9]=2/[C:10]/1=[CH:11]/[C:12]([N:14]1[CH2:15][CH2:16][CH:17]([CH:20]([OH:27])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][CH2:19]1)=[O:13]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 86757749HCID 86757749, compound

Product 2

HCID 70161399HCID 70161399, compoundHCID 86757748HCID 86757748, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 119895722-(Oxolan-2-yl)ethan-1-olSolvent

Procedure

Sodium borohydride (36 mg) was added to a solution of 400 mg of ethyl (Z)-3-(1-{[4,4-difluoro-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]acetyl}-4-piperidyl)-3-oxopropionate in 10 ml of tetrahydrofuran-ethanol (1:1), and the mixture was stirred at room temperature for 28 hours. The reaction solution was diluted with ethyl acetate, washed with a saturated aqueous solution of NaCl and dried over magnesium sulfate, and the solvent was evaporated therefrom. The residue was purified by silica gel column chromatography (eluting with chloroform-methanol). The resulting residue was collected by filtration to give 300 mg of (Z)-1-(1-{[4,4-difluoro-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]acetyl}-4-piperidyl)propane-1,3-diol (29a) as a colorless amorphous solid and 90 mg of ethyl (Z)-3-(1-{[4,4-difluoro-1-(4-methyl-2-phenylthiazole-5-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]acetyl}-4-piperidyl)-3-hydroxypropionate (29b) as a colorless amorphous solid.

Workup

  1. washwashed with a saturated aqueous solution of NaCl
  2. dry with materialdried over magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel column chromatography (eluting with chloroform-methanol)
  5. filtrationThe resulting residue was collected by filtration

Sources & evidence

ORD record
ord-b6c5156ae056412dbe4b2dc3ed80132a
Source dataset
uspto-grants-2002_01
Patent number
US06340678B1

Reaction notes

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