2-adamantyl Chloroformate → Carbonate Ion

HRID 1198066노트

반응식

HRID 1198066 반응식
[CH3:1][C@:2]([C:14]([NH:16][C@H:17]([CH2:25][OH:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:15])([CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)[NH2:3].[CH:27]12[CH2:36][CH:31]3[CH2:32][CH:33]([CH2:35][CH:29]([CH2:30]3)[CH:28]1[O:37][C:38](Cl)=[O:39])[CH2:34]2>C1COCC1.C(OCC)(=O)C>[CH:29]12[CH2:35][CH:33]3[CH2:32][CH:31]([CH2:36][CH:27]([CH2:34]3)[CH:28]1[O:37][C:38](=[O:39])[NH:3][C:2]([CH2:4][C:5]1[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][CH:6]=1)([CH3:1])[C:14]([NH:16][CH:17]([CH2:25][OH:26])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:15])[CH2:30]2.[C:38](=[O:39])([O-:15])[O-:37]

참가 물질

6

반응물 2

HCID 108785372-adamantyl ChloroformateHCID 54471265alpha-methyl-D-tryptophyl-L-phenylalaninol

생성물 2

HCID 19660Carbonate Ion수율 20%HCID 10165354Tricyclo[3.3,1.13,7]dec-2-yl-[2-[[1-(hydroxymethyl)-2-phenylethyl]amino]-1-(1H-indol-3-ylmethyl)-1-methyl-2-oxoethyl]carbamate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

A solution of the α-methyl-D-tryptophyl-L-phenylalaninol (0.5 g, 1.42 mmol) and 4-N,N-dimethylaminopyridine (0.2 g,1.64 mmol), in anhydrous THF (20 mL) was treated dropwise with a solution of 2-adamantylchloroformate (1.4 mmol) in anhydrous THF (20 mL) at room temperature. The reaction was monitored by IR spectroscopy. Once complete, the reaction mixture was diluted with ethyl acetate and washed with 1M citric acid solution, then water. The dried (MgSO4) organic phase was evaporated to dryness and chromatographed over silica using 2% MeOH:98% CH2Cl2 as eluant. This gave the required compound (65% along with 20% carbonate impurity. NOTE: Some of the more acid labile urethanes required chromatography on neutral stationary phases. mp 96°-100° C. (EtOAc-hexane); IR (KBr) 3316, 1695 and 1658 cm-1 ; NMR (CD3OD) δ 1.28 (3H, s), 1.55 (2H, m), 1.68-2.06 (12H, m), 2.76 (2H, ABx, J 13.5 and 17 Hz), 3.31 (2H, Abq, J 14.5 Hz), 3.45 (2H, m), 4.12 (1H, m), 4.78 (1H, br.s) and 6.8-7.5 (10H, m); Anal. (C32H39N3O4), C, H, N.

후처리

  1. washwashed with 1M citric acid solution
  2. dry with materialThe dried (MgSO4) organic phase
  3. customwas evaporated to dryness
  4. customchromatographed over silica using 2% MeOH

출처 및 근거

ORD 기록
ord-c128b85cee724710a92c51f4e92f55fe
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05278316

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