HCID 70913732, compound → HCID 70913730, compound

HRID 1844753Notes

Reaction equation

HRID 1844753 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:28]([CH3:33])([CH3:32])[C:29]([NH2:31])=O)[CH:8]=[C:9]([C:11]2[N:12]([CH2:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[C:13]([CH3:20])=[C:14]([S:16](=[O:19])(=[O:18])[NH2:17])[CH:15]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[NH2:31][CH2:29][C:28]([C:7]1[CH:8]=[C:9]([C:11]2[N:12]([CH2:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[C:13]([CH3:20])=[C:14]([S:16]([NH2:17])(=[O:19])=[O:18])[CH:15]=2)[CH:10]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:6]=1)([CH3:32])[CH3:33]

Participants

3

Reactant 1

HCID 70913732HCID 70913732, compound

Product 1

HCID 70913730HCID 70913730, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of compound 47 (330 mg, 0.70 mol) in dry THF (5 mL) was added a solution of BH3 in THF (1M, 7 mL, 7 mmol) dropwise under cooling with an ice-bath. After the addition, the mixture was stirred at rt overnight, slowly diluted MeOH (5 mL), concentrated and purified by CC (DCM/MeOH=10/1) to give compound 48 (280 mg, 87%) as a white solid. 1H-NMR (DMSO-d6, 400 MHz) δ: 0.64-0.67 (2H, m), 0.89-0.96 (3H, m), 1.21-1.35 (20H, m), 1.46 (3H, d, J=8.0 Hz), 2.44 (3H, s), 3.03 (2H, s), 3.78 (3H, d, J=6.8 Hz), 6.31 (1H, s), 6.93 (2H, s), 7.18 (1H, s), 7.24 (1H, s), 7.37 (1H, s). MS Calcd.: 459; MS Found: 460, (M+1).

Workup

  1. temperatureunder cooling with an ice-bath
  2. additionAfter the addition
  3. concentrationslowly diluted MeOH (5 mL), concentrated
  4. custompurified by CC (DCM/MeOH=10/1)

Sources & evidence

ORD record
ord-db598a5c04374b049b734167fa3d135e
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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