Sodium triacetoxyborohydride → HCID 21978572, compound

HRID 433087Notes

Reaction equation

HRID 433087 reaction equation
[CH2:1]([NH:3][C@@H:4]([CH3:20])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([C:15]2[S:16][CH:17]=[CH:18][N:19]=2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH3:2].[O:21]=[C:22]1[N:28]([CH2:29][CH2:30][CH2:31][CH:32]=O)[CH2:27][CH2:26][CH2:25][O:24][CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]([N:3]([CH:4]([CH3:20])[CH2:5][C:6]1[CH:7]=[CH:8][C:9]([S:12]([C:15]2[S:16][CH:17]=[CH:18][N:19]=2)(=[O:14])=[O:13])=[CH:10][CH:11]=1)[CH2:32][CH2:31][CH2:30][CH2:29][N:28]1[CH2:27][CH2:26][CH2:25][O:24][CH2:23][C:22]1=[O:21])[CH3:2]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 219787184-(3-Oxo-[1,4]oxazepan-4-yl)-butyraldehydeHCID 69223720HCID 69223720, compound

Product 1

HCID 21978572HCID 21978572, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of ethyl-{(S)-1-methyl-2-[4-(thiazole-2-sulfonyl)phenyl]ethyl}-amine (0.326 g, 1.02 mmole), 4-(3-oxo-[1,4]oxazepan-4-yl)-butyraldehyde (0.22 g, 1.2 mmole), and sodium triacetoxyborohydride (0.3 g, 1.4 mmole) in 1,2-dichloroethane (10 mL) was stirred at room temperature for 15 hours. The solvent was removed under reduced pressure and the residue was partitioned between 5% hydrochloric acid and diethyl ether. The aqueous phase was brought to pH 12 with 25% sodium hydroxide and the mixture was extracted with dichloromethane. The organic phase was dried (magnesium sulfate) and concentrated to give 4-(4-{ethyl-[2-(4-thiazole-2-sulfonylphenyl)-1-methylethyl]amino}butyl)-[1,4]oxazepan-3-one, 145, as an oil. Anal.: Calcd. for C23H34ClN3O4S2.1H2O: C, 51.72; H, 6.79; N, 7.87%; Found C, 51.71; H, 6.49 N 7.82%.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between 5% hydrochloric acid and diethyl ether
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe organic phase was dried (magnesium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-19eae569294d46df9c202a048394e14e
Source dataset
uspto-grants-2003_12
Patent number
US06667301B2

Reaction notes

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