Hydrogen Bromide → HCID 54499178, compound

HRID 1085014Notes

Reaction equation

HRID 1085014 reaction equation
C([O:3][P:4]([CH2:24][NH:25][C:26](=[O:62])[C@H:27]([CH2:58][CH:59]([CH3:61])[CH3:60])[NH:28][C:29](=[O:57])[C@@H:30]([NH:46][C:47]([O:49][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:48])[CH2:31][CH2:32][CH2:33][CH2:34][N:35]1[C:39](=[O:40])[C:38]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:37]2[C:36]1=[O:45])([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.Br.ClC(OCC1C=CC=CC=1)=O>C(O)(=O)C.C(=O)([O-])O.[K+]>[CH2:50]([O:49][C:47]([NH:46][C@@H:30]([CH2:31][CH2:32][CH2:33][CH2:34][N:35]1[C:36](=[O:45])[C:37]2=[CH:44][CH:43]=[CH:42][CH:41]=[C:38]2[C:39]1=[O:40])[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]([CH3:17])[CH3:18])[CH2:8][CH:9]([CH3:10])[CH3:11])(=[O:3])[OH:5])=[O:62])[CH2:58][CH:59]([CH3:61])[CH3:60])=[O:57])=[O:48])[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 10387Benzyl chloroformateHCID 54009497HCID 54009497, compound

Product 1

HCID 54499178HCID 54499178, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 516893Potassium BicarbonateSolvent

Procedure

0.6 g of [[[N-[(S)-2-[1-(benzyloxy)formamido]-6-phthalimidohexanoyl]-L-leucyl]amino]methyl][(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid ethyl ester was dissolved in 2 ml of acetic acid and 2 ml of 45% hydrogen bromide in acetic acid and left to stand at room temperature overnight. The solvent was removed by evaporation and the residue was re-evaporated with toluene until a solid was obtained. This solid was dissolved in aqueous potassium hydrogen carbonate solution, 0.14 ml of benzyl chloroformate was added and the mixture was stirred for 4 hours. The solution was extracted twice with diethyl ether and acidified with hydrochloric acid. The solid was separated and dissolved by extraction with hot chloroform. The organic solution was dried over anhydrous magnesium sulfate and evaporated to yield 0.53 g of [[[N-[(S)-2-[1-(benzyloxy)formamido]-6-phthalimidohexanoyl]-L-leucyl]amino]methyl][(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid in the form of an amorphous cream powder.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was re-evaporated with toluene until a solid
  3. customwas obtained
  4. extractionThe solution was extracted twice with diethyl ether
  5. customThe solid was separated
  6. dissolutiondissolved by extraction with hot chloroform
  7. dry with materialThe organic solution was dried over anhydrous magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-ff73a2d239244780bec75ba03b7c0275
Source dataset
uspto-grants-1991_04
Patent number
US05006651

Reaction notes

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