Diethyl Ether → HCID 54061511, compound

HRID 1085013Notes

Reaction equation

HRID 1085013 reaction equation
C([O:3][P:4]([CH2:24][NH:25][C:26](=[O:48])[C@H:27]([CH2:44][CH:45]([CH3:47])[CH3:46])[NH:28][C:29](=[O:43])[C@@H:30]1[CH2:34][CH2:33][CH2:32][N:31]1[C:35](=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([CH2:6][CH:7]([C:12](=[O:23])[NH:13][C@H:14]([C:19](=[O:22])[NH:20][CH3:21])[CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:8][CH:9]([CH3:11])[CH3:10])=[O:5])C.C(OCC)C>C(O)(=O)C.Br>[C:35]([N:31]1[CH2:32][CH2:33][CH2:34][C@H:30]1[C:29]([NH:28][C@H:27]([C:26]([NH:25][CH2:24][P:4]([CH2:6][CH:7]([C:12](=[O:23])[NH:13][C@H:14]([C:19](=[O:22])[NH:20][CH3:21])[CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:8][CH:9]([CH3:10])[CH3:11])(=[O:3])[OH:5])=[O:48])[CH2:44][CH:45]([CH3:47])[CH3:46])=[O:43])(=[O:42])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 53871092HCID 53871092, compound

Product 1

HCID 54061511HCID 54061511, compoundYield 70.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 260Hydrogen BromideSolvent

Procedure

0.25 g of [[[N-(1-benzoyl-L-prolyl)-L-leucyl]amino]methyl][(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid ethyl ester was dissolved in a mixture of 1 ml of acetic acid and 1 ml of 45% hydrogen bromide in acetic acid and the mixture was left to stand at room temperature overnight. The solution was treated with diethyl ether. The precipitated gum was allowed to settle and the ethereal solution was removed by decantation. Further treatment with diethyl ether followed by dichloromethane and subsequent drying in a high vacuum yielded 0.17 g of [[[N-(1-benzoyl-L-prolyl)-L-leucyl] amino]methyl][(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid in the form of a light brown foam containing some hydrogen bromide.

Workup

  1. waitthe mixture was left
  2. customthe ethereal solution was removed by decantation
  3. customsubsequent drying in a high vacuum

Sources & evidence

ORD record
ord-55ca5b426c7d4deabc85b043cac1bddb
Source dataset
uspto-grants-1991_04
Patent number
US05006651

Reaction notes

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