Piperidine → Phenylmethyl [6-[1-piperidinyl]-5-[[(4-methylphenyl)sulfony]amino]-6-oxohexyl]carbamate

HRID 1728778

反応式

HRID 1728778 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[C:13](O)=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C)C=O>[N:38]1([C:13](=[O:14])[CH:12]([NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)(=[O:9])=[O:10])[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:22])[O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1

参加物

6

反応物 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 140824522-[[(4-Methylphenyl)sulfonyl]amino]-6-[[(phenylmethoxy)carbonyl]amino]hexanoic acid

生成物 1

HCID 54493764Phenylmethyl [6-[1-piperidinyl]-5-[[(4-methylphenyl)sulfony]amino]-6-oxohexyl]carbamate収率 100.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a cold (0° C.), nitrogen-blanketed mixture of 2-[[(4-methylphenyl]sulfonyl]amino]6-[[(phenylmethoxy)carbonyl]amino]hexanoic acid (18.00g, 44.43 mmol), triethylamine (5.80 mL, 41.43 mmol) and piperidine (4.10 mL, 41.43 mmol) in anhydrous dimethylformamide (80 mL) was added dropwise diphenylphosphoryl azide (8.90 mL, 41.43 mmol). The mixture was stirred at about 0° C. for about 1 hour and at ambient temperature for about 2 hours before it was partitioned between ethyl acetate and water. The organic phase was separated and the aqueous phase was extracted three additional times with ethyl acetate. The combined extracts were then washed with saturated sodium bicarbonate solution, 1N hydrochloric acid and brine prior to drying and solvent concentration. There was isolated in sufficiently pure state 20.90g (100%) of the title compound of as pale yellow oil; 1H NMR (CDCl3) δ 7.62 (d, J=8.2 Hz, 2H), 7.30-7.22 (m, 5H), 7.19 (d, J=8.1 Hz, 2H), 5.94 (d, J=8.9 Hz, 1H), 5.09-5.07 (m, 1H), 5.03 (s, 2H), 3.90-3.88 (m, 1H), 3.43-3.36 (m, 1H), 3.09-2.91 (m, 5H), 2.32 (s, 3H), 1.43-1.23 (m, 10H), 1.09-0.97 (m, 2H); 13C NMR (CDCl3) ppm 168.28, 156.09, 142.87, 136.43, 136.30, 128.98, 127.95, 127.43, 126.96, 65.81, 52.08, 45.70, 42.67, 40.14, 32.58, 28.72, 25.49, 24.65, 23.64, 21.71, 20.93; IR (KBr, cm-1) 3316, 2938, 2860, 1718, 1634, 1526, 1452, 1416, 1340, 1246, 1162, 1092; MS m/z (MH+) calcd 502.2376, obsd 502.2363.

後処理

  1. customwas partitioned between ethyl acetate and water
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted three additional times with ethyl acetate
  4. washThe combined extracts were then washed with saturated sodium bicarbonate solution, 1N hydrochloric acid and brine
  5. customto drying
  6. concentrationsolvent concentration

出典と根拠

ORDレコード
ord-2ca96f38c38c48ab8b873d5c954883a2
出典データセット
uspto-grants-1994_07
特許番号
US05328932

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