Ethylmorpholine → (S)-1-(tert-Butyl)pyrrolidine-2-carboxamide

HRID 54090

反応式

HRID 54090 の反応式
N#N.N[C@@H](CC1C=CC=CC=1)[C@H](O)C[C@@:7]1([C:16]([NH2:18])=[O:17])[CH2:11][CH2:10][CH2:9][N:8]1[C:12]([CH3:15])([CH3:14])[CH3:13].C(OC(N[C@H](C(O)=O)CSC)=O)C1C=CC=CC=1.OC1C2N=NNC=2C=CC=1.C(N1CCOCC1)C.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.C(OCC)(=O)C>[C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:16]([NH2:18])=[O:17])([CH3:15])([CH3:13])[CH3:14]

参加物

8

反応物 5

HCID 7525EthylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 57121652N-((Benzyloxy)carbonyl)-S-methyl-L-cysteineHCID 86746262N2 [3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1 tert.butyl-L-prolinamideHCID 178418300HCID 178418300、化合物

生成物 1

HCID 54424267(S)-1-(tert-Butyl)pyrrolidine-2-carboxamide

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 650 mg of N2 -[3(S)-amino-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide and 538 mg of N-(benzyloxycarbonyl)-S-methyl-L-cysteine in 20 ml of dry tetrahydrofuran was cooled in an ice/salt mixture. 270 mg of hydroxybenzotriazole, 230 mg of N-ethylmorpholine and 412 mg of dicyclohexylcarbodiimide were added and the mixture was stirred for 16 hours. The mixture was diluted with ethyl acetate and filtered. The filtrate was washed with aqueous sodium bicarbonate solution and sodium chloride solution. The solvent was removed by evaporation and the residue was chromatographed on silica gel using System G for the elution to give 800 mg of N2 -[3(S)-[N-(benzyloxycarbonyl)-S-methyl-L-cysteinyl]amino]-2(R)-hydroxy-4-phenylbutyl]-N1 -tert.butyl-L-prolinamide; MS: m/e 585 [M+H]+.

後処理

  1. filtrationfiltered
  2. washThe filtrate was washed with aqueous sodium bicarbonate solution and sodium chloride solution
  3. customThe solvent was removed by evaporation
  4. customthe residue was chromatographed on silica gel using System G for the elution

出典と根拠

ORDレコード
ord-ad973eb644d44f46a9641b14118382e9
出典データセット
uspto-grants-1997_04
特許番号
US05620987

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