Hydrogen Bromide → HCID 19070477, compound

HRID 1955685Notes

Reaction equation

HRID 1955685 reaction equation
C(OC([NH:11][CH:12]([S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])=[O:22])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O)C1C=CC=CC=1.[BrH:30]>C(O)(=O)C.CCOCC>[BrH:30].[NH2:11][CH:12]([S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])=[O:22])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 10597651Carbamic acid, [3-phenyl-1-(phenylsulfonyl)propyl]-, phenylmethyl ester

Product 1

HCID 19070477HCID 19070477, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

Method A: Z-Hph-α-SO2Ph (1.0 g, 2.44 mmol) was treated with 30% hydrogen bromide in acetic acid (5 mL). After 30 minutes, the mixture was diluted with ether (300 mL), filtered, washed with ether (2×30 mL), and dried in vacuo to give 0.74 g (86%) 1-amino-3-phenyl-1-phenylsulfonylpropane hydrobromide (HBr.Hph-α-SO2Ph). To a solution of Mu-PheOH (0.64 g, 2.3 mmol) in THF (15 mL) were added 4-methylmorpholine (0.302 mL, 2.3 mmol) and isobutyl chloroformate (0.312 mL, 2.3 mmol). The mixture was stirred for 10 minutes. HBr.Hph-α-SO2Ph (0.74 g, 2.1 mmol) was added, followed by 4-methylmorpholine (0.302 mL, 2.3 mmol). After 45 minutes, the mixture was diluted with ethyl acetate (30 mL), washed with 15 mL each of 1M HCl, saturated aqueous sodium bicarbonate, and brine, dried over MgSO4, filtered, and the solvent was removed under reduced pressure to give 0.75 g (65%) of the product, Mu-Phe-Hph-α-SO2Ph.

Workup

  1. filtrationfiltered
  2. washwashed with ether (2×30 mL)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-2690197b60204f74bbfdf6ae6c9f8750
Source dataset
uspto-grants-1998_07
Patent number
US05776718

Reaction notes

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