Triethylamine → {2-[(2-Amino-benzothiazole-6-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester

HRID 416240

反応式

HRID 416240 の反応式
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11]([OH:13])=O)[CH:8]=[CH:7][C:5]=2[N:6]=1.[C:14]([O:18][C:19](=[O:28])[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[NH2:27])([CH3:17])([CH3:16])[CH3:15].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(CC)CC>CN(C=O)C>[C:14]([O:18][C:19](=[O:28])[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[NH:27][C:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH2:1])[S:3][C:4]=2[CH:10]=1)=[O:13])([CH3:17])([CH3:15])[CH3:16]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 667406-Benzothiazolecarboxylic acid, 2-amino-HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamine

生成物 1

HCID 58930649{2-[(2-Amino-benzothiazole-6-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester収率 52%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The acid 114 (1.80 g, 9.27 mmol) was combined with (2-amino-phenyl)-carbamic acid tert-butyl ester (2.31 g, 11.1 mmol) and BOP (4.91 g, 11.1 mmol) in DMF. To this solution Et3N (5.16 ml, 37.1 mmol) was added and the mixture was stirred overnight at room temperature under nitrogen, concentrated in vacuo and purified by flash column chromatography (30% hexane/EtOAc). To further purify the product, the mixture was partitioned between EtOAc and water, organic layer was separated, dried over MgSO4 and evaporated give the title compound 115 (1.84 g, 52%). 1H-NMR (DMSO) δ: 9.72 (s, 1H), 8.66 (m, 1H); 8.22 (d, J=1.8 Hz, 1H); 7.80 (m, 3H); 7.50 (m, 2H); 7.37 (m, 1H); 7.14 (m, 2H); 1.44 (s, 9H).

後処理

  1. concentrationconcentrated in vacuo
  2. custompurified by flash column chromatography (30% hexane/EtOAc)
  3. customTo further purify the product
  4. customthe mixture was partitioned between EtOAc and water, organic layer
  5. customwas separated
  6. dry with materialdried over MgSO4
  7. customevaporated

出典と根拠

ORDレコード
ord-43b2456e5de046fb85e66de78ee4d9a1
出典データセット
uspto-grants-2012_01
特許番号
US08088805B2

関連ノート

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