Triethylamine → benzyl N-[(2S)-4-[(2S)-2-[[(2S,3S)-3-methyl-1-(2-methylpropylamino)-1-oxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-3-oxo-1-phenylbutan-2-yl]carbamate;molecular nitrogen

HRID 466829Notes

Reaction equation

HRID 466829 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([CH2:22]Br)=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:24]#[N:25].[NH:26]1[CH2:45][CH2:44][CH2:43][C@H:27]1[C:28]([NH:30][C@H:31]([C:36]([NH:38][CH2:39][CH:40]([CH3:42])[CH3:41])=[O:37])[C@H:32]([CH2:34][CH3:35])[CH3:33])=[O:29].C(N(CC)CC)C>ClCCl>[N:24]#[N:25].[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:20]([CH2:22][N:26]1[CH2:45][CH2:44][CH2:43][C@H:27]1[C:28]([NH:30][C@H:31]([C:36]([NH:38][CH2:39][CH:40]([CH3:41])[CH3:42])=[O:37])[C@H:32]([CH2:34][CH3:35])[CH3:33])=[O:29])=[O:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11383290Benzyloxycarbon-yl-l-phenylalanylbromomethaneHCID 86746218N2 L-prolyl-N1-isobutyl-L-isoleucinamide

Product 1

HCID 86746217benzyl N-[(2S)-4-[(2S)-2-[[(2S,3S)-3-methyl-1-(2-methylpropylamino)-1-oxopentan-2-yl]carbamoyl]pyrrolidin-1-yl]-3-oxo-1-phenylbutan-2-yl]carbamate;molecular nitrogen

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 8.86 g of [N-(benzyloxycarbonyl)-L-phenylalanyl]methyl bromide 6.71 g of N2 -L-prolyl-N1 -isobutyl-L-isoleucinamide and 2.60 g of triethylamine in 400 ml of dichloromethane was stirred at room temperature overnight. The solvent was removed by evaporation and the crude product was chromatographed on silica gel using ethyl acetate for the elution. The resulting product was triturated with a mixture of petroleum ether (b.p. 40°-60° C.) and ethyl acetate to give 8.70 g of N2 -[N-[[N-(benzyloxycarbonyl)-L-phenylalanyl]methyl]-L-prolyl]-N1 -isobutyl-L-isoleucinamide as an off-white solid of m.p. 80°-81° C.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe crude product was chromatographed on silica gel
  3. washfor the elution
  4. customThe resulting product was triturated with a mixture of petroleum ether (b.p. 40°-60° C.) and ethyl acetate

Sources & evidence

ORD record
ord-678708d3fd184aa08addd504778814f9
Source dataset
uspto-grants-1992_10
Patent number
US05157041

Reaction notes

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