4-Methylmorpholine → HCID 23511717、化合物

HRID 1968427ノート

反応式

HRID 1968427 の反応式
[C:1]([O:5][C:6]([N:8]1[CH:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:10][CH:9]1C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CN1CCOCC1.C1(NC(=O)C(O)C(N)CCC)CC1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 79724-Methylmorpholine2 回HCID 2724699PyBOPHCID 47125101-(tert-Butoxycarbonyl)octahydro-1H-indole-2-carboxylic acidHCID 208049823-Amino-N-cyclopropyl-2-hydroxyhexanamide

生成物 1

HCID 23511717HCID 23511717、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

Octahydro-indole-1,2-dicarboxylic acid 1-tert-butyl ester 89 (Bachem, 1.6 g, 1.0 eq) in DMF (20 mL) was treated with PyBOP (3.41 g, 1.1 eq) and NMM (1.97 mL, 3.0 eq). To this was added 3-amino-2-hydroxy-hexanoic acid cyclopropylamide 90 (1.22 g, 1.1 eq, prepared according to the procedure of U. Schoellkogf et al., Justus Liebigs Ann. Chem. GE, pp. 183-202 (1976) and J. Semple et al., Org. Letters, 2, pp. 2769-2772 (2000) and NMM (1.97 mL, 3.0 eq) in DMF (3 mL) and the mixture stirred at rt overnight. The mixture was evaporated in vacuo, diluted with ethyl acetate, the organic phase washed with 0.5N HCl, sodium bicarbonate and brine, then dried over sodium sulfate, filtered and concentrated in vacuo to give 2-[1-cyclopropylcarbamoyl-hydroxy-methyl)-butylcarbamoyl]-octahydro-indole-1-carboxylic acid tert-butyl ester 91 which was used without further purification. 1H NMR (CDCl3) δ 6.92 (bs, 1H), 6.80 (bs, 1H), 3.80-4.20 (m, 3H), 2.75 (m, 1H), 2.25 (m, 1H), 2.10 (m, 1H), 1.90-2.00 (m, 2H), 1.5-1.75 (m, 7H), 1.45 (s, 9H), 1.10-1.40 (m, 5H), 0.90 (m, 3H), 0.75 (m, 2H), 0.50 (m, 2H) ppm.

後処理

  1. customprepared
  2. customThe mixture was evaporated in vacuo
  3. additiondiluted with ethyl acetate
  4. washthe organic phase washed with 0.5N HCl, sodium bicarbonate and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-ba51ed510c744e09b47609790bab4323
出典データセット
uspto-grants-2013_04
特許番号
US08426359B2

反応ノート

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