1,2-Dichloroethane → N-[(1R)-1-[(Benzylsulfonyl)methyl]-2-{[(1S)-1-methyl-2-{[4-(trifluoromethoxy)phenyl]amino}ethyl]amino}-2-oxoethyl]morpholine-4-carboxamide

HRID 2249950ノート

反応式

HRID 2249950 の反応式
[N:1]1([C:7]([NH:9][C@@H:10]([CH2:14][S:15]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:17])=[O:16])[C:11]([OH:13])=O)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F:25][C:26]([F:40])([F:39])[O:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][CH2:35][C@@H:36]([NH2:38])[CH3:37])=[CH:30][CH:29]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl>[CH3:37][C@H:36]([NH:38][C:11]([C@@H:10]([NH:9][C:7]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[O:8])[CH2:14][S:15]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:17])=[O:16])=[O:13])[CH2:35][NH:34][C:31]1[CH:30]=[CH:29][C:28]([O:27][C:26]([F:25])([F:39])[F:40])=[CH:33][CH:32]=1

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 11439693(R)-2-[(morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionic acidHCID 59733160HCID 59733160、化合物

生成物 1

HCID 9547980N-[(1R)-1-[(Benzylsulfonyl)methyl]-2-{[(1S)-1-methyl-2-{[4-(trifluoromethoxy)phenyl]amino}ethyl]amino}-2-oxoethyl]morpholine-4-carboxamide収率 31%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-(R)-[(Morpholine-4-carbonyl)-amino]-3-phenylmethanesulfonyl-propionic acid (73 mg, 0.21 mmol, 1.0 eq.), N1-(4-Trifluoromethoxy-phenyl)-(S)-propane-1,2-diamine from Scheme 1a (48 mg, 0.21 mmol, 1.0 eq.), EDC (59 mg, 0.31 mmol, 1.5 eq.), and HOBT (38 mg, 0.25 mmol, 1.2 eq.) were dissolved in CH2Cl2 at room temperature. N-methylmorpholine (225 μL, 2.05 mmol, 10 eq.) was added via syringe and the reaction was monitored to completion by LC/MS. The solvent was evaporated and the reaction was purified by mass-directed HPLC and provided 44 mg (0.06 mmol, 31%) of a off-white solid as a mono-TFA salt: HPLC-MS calcd. for C25H31F3N4O6S (M+H+) 573.2. found 573.3.

後処理

  1. customThe solvent was evaporated
  2. customthe reaction was purified by mass-directed HPLC

出典と根拠

ORDレコード
ord-9fc8da570b0f4fd9aecd49e14bce698e
出典データセット
uspto-grants-2008_01
特許番号
US07314872B2

反応ノート

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