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Dimethylamine → 3beta-tert-butyidimethylsilyloxy-4,4-dimethyl-5alpha-chola-8,14-dien-24 oic acid-N,N-dimethyl amide

HRID 479307
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HRID 479307 반응식
[Si:1]([O:8][C@H:9]1[CH2:32][CH2:31][C@@:30]2([CH3:33])[C@@H:11]([CH2:12][CH2:13][C:14]3[C:15]4[C@:26]([CH3:34])([CH2:27][CH2:28][C:29]=32)[C@@H:18]([C@H:19]([CH3:25])[CH2:20][CH2:21][C:22]([OH:24])=O)[CH2:17][CH:16]=4)[C:10]1([CH3:36])[CH3:35])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:37][N:38]1CCOC[CH2:39]1.C(OC(Cl)=O)C(C)C.CNC>ClCCl.C1COCC1>[CH3:37][N:38]([CH3:39])[C:22](=[O:24])[CH2:21][CH2:20][C@H:19]([C@@H:18]1[C@:26]2([CH3:34])[C:15]([C:14]3[CH2:13][CH2:12][C@@H:11]4[C@:30]([C:29]=3[CH2:28][CH2:27]2)([CH3:33])[CH2:31][CH2:32][C@H:9]([O:8][Si:1]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2])[C:10]4([CH3:36])[CH3:35])=[CH:16][CH2:17]1)[CH3:25]
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7

반응물 4

HCID 674DimethylamineHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 694107953beta-Tert-butyidimethylsilyloxy-4,4-dimethyl-5alpha-chola-8,14-dien-24 oic acid

생성물 1

HCID 1317242073beta-tert-butyidimethylsilyloxy-4,4-dimethyl-5alpha-chola-8,14-dien-24 oic acid-N,N-dimethyl amide

시약·촉매·용매 2

HCID 6344Dichloromethane용매
HCID 8028Tetrahydrofuran용매

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온도
-15 °C

실험 절차

3β-tert-butyldimethylsilyloxy-4,4-dimethyl-5α-chola-8,14-dien-24 oic acid (0.30 g) is dissolved in 10 ml of dry dichloromethane. After cooling to −15° C., 0.07 ml of N-methylmorpholine and 0.084 ml of isobutylchloroformate is added and the mixture is stirred at −15° C. for 20 minutes, whereupon 1.74 ml of a 2.0 M solution of N,N-dimethylamine in THF) is added. The mixture is stirred overnight and the temperature is slowly elevated to room temperature. After aqueous work-up and crystallization from methanol, 3β-tert-butyldimethylsilyloxy-4,4-dimethyl-5α-chola-8,14-dien-24 oic acid-N,N-dimethyl amide (0,231 g) is obtained. M.p. 143-145° C. 1H-NMR (CDCl3, 400 MHz)): δ=5.35 (1H, s); 3.20 (1H, m); 3.03 (3H, s); 2.95 (3H, s); 0.90 (9H, s); 0.05 (6H, m).

후처리

  1. additionis added
  2. customis slowly elevated to room temperature
  3. customAfter aqueous work-up and crystallization from methanol

출처 및 근거

ORD 기록
ord-92aa0eff81444bb7a558a06a703d6734
출처 데이터셋
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06645953B2

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