Sodium borohydride → HCID 54767336, compound

HRID 1503291Notes

Reaction equation

HRID 1503291 reaction equation
[BH4-].[Na+].[C:3]([C:5]1[CH:6]=[C:7]([CH:34]=[CH:35][C:36]=1[C:37]([F:40])([F:39])[F:38])[O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([C:24](=[O:33])[C:25]([NH:27][CH2:28][C@H:29]([OH:32])[CH2:30][OH:31])=[O:26])=[CH:16]2)=[CH:11][CH:10]=1)#[N:4]>CCO.C1COCC1>[C:3]([C:5]1[CH:6]=[C:7]([CH:34]=[CH:35][C:36]=1[C:37]([F:40])([F:39])[F:38])[O:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([CH:24]([OH:33])[C:25]([NH:27][CH2:28][C@H:29]([OH:32])[CH2:30][OH:31])=[O:26])=[CH:16]2)=[CH:13][CH:14]=1)#[N:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 54767169HCID 54767169, compound

Product 1

HCID 54767336HCID 54767336, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

NaBH4 (20 mg) was added to a solution of compound 68 (50 mg) in EtOH/THF (2 mL/2 mL) at room temperature, and the mixture was shaken at room temperature for 1 hour. The reaction was quenched with water, extracted with EtOAc (30 mL), concentrated, and purified by column (CHCl3/MeOH 10/1.5) to give compound 69 as a white solid (40 mg, 40%): 1H-NMR (400 MHz, CD3OD): δ 7.72-7.76 (m, 2H), 7.49-7.53 (m, 2H), 7.3-7.46 (m, 4H), 7.05-7.21 (m, 4H), 5.35-5.37 (m, 1H), 3.67-3.73 (m, 1H), 3.43-3.47 (m, 3H), 3.28-3.32 (m, 1H); LC/MS: m/z=548.2 [M+Na]+ (Calc: 525.4).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with EtOAc (30 mL)
  3. concentrationconcentrated
  4. custompurified by column (CHCl3/MeOH 10/1.5)

Sources & evidence

ORD record
ord-66c0ff0fa2004b4f84781d7c70cc1ce0
Source dataset
uspto-grants-2015_12
Patent number
US09212139B2

Reaction notes

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