Ammonia → {4-[4-(3-Amino-2-hydroxypropoxy)phenyl]butyl}carbamic acid benzyl ester

HRID 889860Notes

Reaction equation

HRID 889860 reaction equation
[CH2:1]([O:8][C:9](=[O:26])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]2[CH2:25][O:24]2)=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:27]>C(O)C>[CH2:1]([O:8][C:9](=[O:26])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH:23]([OH:24])[CH2:25][NH2:27])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 85988461[4-(4-Oxiranylmethoxyphenyl)butyl]carbamic acid benzyl ester

Product 1

HCID 68647372{4-[4-(3-Amino-2-hydroxypropoxy)phenyl]butyl}carbamic acid benzyl esterYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

An ethanol solution of 39 (0.86 g, 2.42 mmol) was saturated with ammonia and stirred overnight at room temperature. The solvent was evaporated and the residue was purified by Flash™ (BIOTAGE, Inc) (90 g silica gel cartridge 40M, 6:1:0.1 chloroform/ethanol/concentrated ammonium hydroxide) to provide 40 (0.75 g, 87%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 1.40 (m, 2H), 1.51 (m, 2H), 2.50 (m, 2H), 2.58 (m, 1H), 2.68 (m, 1H), 3.00 (m, 2H), 3.69 (m, 1H), 3.80 (m, 1H), 3.90 (m, 1H), 5.08 (s, 2H), 6.82 (d, 2H), 7.06 (d, 2H), 7.35 (br s, 5H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by Flash™ (BIOTAGE, Inc) (90 g silica gel cartridge 40M, 6:1:0.1 chloroform/ethanol/concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-3e77bcdec71f4475b15cd9c2f96efa90
Source dataset
uspto-grants-2006_02
Patent number
US06995160B2

Reaction notes

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