Ethylmorpholine → (R)-N-[(RS)-1-amidino-3-piperidinylmethyl]-alpha(2-naphthylsulfonamido)indole-3-propionamide bisulfite

HRID 1081193노트

반응식

HRID 1081193 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([NH:14][C@@H:15]([C:26](O)=[O:27])[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)(=[O:13])=[O:12].C(N1CCOCC1)C.[S:37]([OH:40])([OH:39])=[O:38].[NH2:41][CH2:42][CH:43]1[CH2:48][CH2:47][CH2:46][N:45]([C:49](=[NH:51])[NH2:50])[CH2:44]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[S:37](=[O:38])([OH:40])[OH:39].[C:49]([N:45]1[CH2:46][CH2:47][CH2:48][CH:43]([CH2:42][NH:41][C:26](=[O:27])[C@H:15]([NH:14][S:11]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)(=[O:13])=[O:12])[CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)[CH2:44]1)(=[NH:50])[NH2:51]

참가 물질

6

반응물 4

HCID 7525EthylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 1800786(R)-3-(1H-Indol-3-yl)-2-(naphthalene-2-sulfonylamino)-propionic acidHCID 19080933Rac-3aminomethyl-1-amidinopiperidine sulphite

생성물 1

HCID 22848479(R)-N-[(RS)-1-amidino-3-piperidinylmethyl]-alpha(2-naphthylsulfonamido)indole-3-propionamide bisulfite수율 44.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 1.5 g of N-(2-naphthylsulfonyl)-D-tryptophan in 30 ml of DMF is treated with 1.5 ml of ethylmorpholine. After the addition of 0.7 g of rac-3-aminomethyl-1-amidinopiperidine sulphite (Example 1) and 1.7 g of benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate the reaction mixture is stirred for 15 hours. The solvent is evaporated and the residue is taken up in 50 ml of water and extracted with 100 ml of ethyl acetate. The ethyl acetate phase is washed with water, dried and evaporated. The crude material is purified on a RP-18 column with water/acetonitrile (0-30%). There is obtained 0.8 g of (R)--N--[(RS)-1-amidino-3-piperidinylmethyl]-α(2-naphthylsulfonamido)indole-3-propionamide bisulfite, FAB-MS: 533 (M+H)+.

후처리

  1. customThe solvent is evaporated
  2. extractionextracted with 100 ml of ethyl acetate
  3. washThe ethyl acetate phase is washed with water
  4. customdried
  5. customevaporated
  6. customThe crude material is purified on a RP-18 column with water/acetonitrile (0-30%)

출처 및 근거

ORD 기록
ord-eb29787874014f968d74caf27cf4ad32
출처 데이터셋
uspto-grants-1996_12
특허 번호
US05583133

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