Water → HCID 69940593, compound

HRID 1058763Notes

Reaction equation

HRID 1058763 reaction equation
[OH:1][P:2]([CH2:23][CH:24]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:25]([NH:27][C@H:28]([C:30]([OH:32])=[O:31])[CH3:29])=[O:26])([CH:4]([NH:12]C(OCC1C=CC=CC=1)=O)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].B(Br)(Br)[Br:41].O>ClCCl>[BrH:41].[NH2:12][CH:4]([P:2]([CH2:23][CH:24]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:25]([NH:27][C@H:28]([C:30]([OH:32])=[O:31])[CH3:29])=[O:26])([OH:3])=[O:1])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 15383288HCID 15383288, compound

Product 1

HCID 69940593HCID 69940593, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a solution of 50 mg (0.09 mmol) of N-[2-[[hydroxy[2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinyl]methyl]-1-oxo-3-phenylpropyl]-L-alanine in 2.5 ml of dichloromethane, cooled to −10° C., is added, under nitrogen, 0.45 ml of boron tribromide as a 1M solution in dichloromethane (0.45 mmol). The mixture is stirred for one hour at −10° C. and then for two hours at a temperature in the region of 20° C. 3 ml of water are added and the dichloromethane is evaporated off. The aqueous phase is washed with diethyl ether and evaporated to dryness. The product is taken up in water and then freeze-dried. 45 mg of product are recovered (yield=100%).

Workup

  1. additionis added, under nitrogen
  2. waitfor two hours at a temperature in the region of 20° C
  3. customthe dichloromethane is evaporated off
  4. washThe aqueous phase is washed with diethyl ether
  5. customevaporated to dryness
  6. customfreeze-dried
  7. custom45 mg of product are recovered (yield=100%)

Sources & evidence

ORD record
ord-ab51da11c51c4eb1afd7d0172c93190a
Source dataset
uspto-grants-2003_02
Patent number
US06518260B1

Reaction notes

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