Boron tribromide → (R)-4-(1-amino-3-hydroxy-1-oxopropan-2-ylamino)-2-(3-methylisothiazol-5-ylamino)benzamide

HRID 84822Notes

Reaction equation

HRID 84822 reaction equation
[NH2:1][C:2](=[O:30])[C@H:3]([NH:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[C:16]([NH:23][C:24]2[S:28][N:27]=[C:26]([CH3:29])[CH:25]=2)[CH:15]=1)[CH2:4][O:5]CC1C=CC=CC=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:1][C:2](=[O:30])[C@H:3]([NH:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[C:16]([NH:23][C:24]2[S:28][N:27]=[C:26]([CH3:29])[CH:25]=2)[CH:15]=1)[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57334483(R)-4-(1-amino-3-(benzyloxy)-1-oxopropan-2-ylamino)-2-(3-methylisothiazol-5-ylamino)benzamide

Product 1

HCID 57334484(R)-4-(1-amino-3-hydroxy-1-oxopropan-2-ylamino)-2-(3-methylisothiazol-5-ylamino)benzamideYield 33.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (R)-4-(1-amino-3-(benzyloxy)-1-oxopropan-2-ylamino)-2-(3-methylisothiazol-5-ylamino)benzamide (4 mg, 0.009 mmol) in CH2Cl2 (1 mL), BBr3 (0.050 mL, 0.53 mmol) was added. After being stirred and swirled for 1 h, the mixture was purified by HPLC to give the titled compound (1 mg). MS 336.3 (M+H); UV 202.9, 294.6 nm

Workup

  1. additionwas added
  2. customthe mixture was purified by HPLC

Sources & evidence

ORD record
ord-900addc5cf65460c956d6a368b416de1
Source dataset
uspto-grants-2014_09
Patent number
US08846928B2

Reaction notes

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