Benzyl Alcohol → Benzyl 5-[(1-tert-butoxyformamido)methyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate

HRID 2395145노트

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HRID 2395145 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[C:20]2[C:11]=1[O:12][C:13]1[C:14]([CH2:30][C:31]([OH:33])=[O:32])=[C:15]([O:28][CH3:29])[CH:16]=[CH:17][C:18]=1[C:19]2([CH3:27])[CH3:26])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:34](O)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[C:20]2[C:11]=1[O:12][C:13]1[C:14]([CH2:30][C:31]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:32])=[C:15]([O:28][CH3:29])[CH:16]=[CH:17][C:18]=1[C:19]2([CH3:26])[CH3:27])=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 3

HCID 244Benzyl AlcoholHCID 10868DicyclohexylcarbodiimideHCID 676449095-[(1-Tert-butoxyformamido)methyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetic acid

생성물 1

HCID 67645989Benzyl 5-[(1-tert-butoxyformamido)methyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate수율 80.8%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

A solution of 3 g (6.55 mmol) of 5-[(1-tert-butoxyformamido)methyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetic acid in 65 ml of methylene chloride was cooled to 20° and treated with 1.1 ml (10.62 mmol) of benzyl alcohol. After the addition of 20 mg of 4-dimethylaminopyridine a solution of 1.5 g (7.27 mmol) of dicyclohexylcarbodiimide in 16 ml of methylene chloride was added dropwise, whereupon the mixture was warmed to room temperature and was stirred for 3 hours. The precipitated dicyclohexylurea was filtered off and washed with a small amount of methylene chloride. The filtrate was washed with sodium bicarbonate solution and water, dried over sodium sulphate and concentrated. The residue remaining was chromatographed on silica gel with hexane/ethyl acetate, whereby 2.9 g of benzyl 5-[(1-tert-butoxyformamido)methyl]-3,6-dimethoxy-9,9-dimethylxanthene-4-acetate were obtained as a colourless powder m.p. of 139°-141°; IR 3443, 2972, 2930, 1724, 1605, 1498 cm-1.

후처리

  1. additionwas added dropwise, whereupon the mixture
  2. filtrationThe precipitated dicyclohexylurea was filtered off
  3. washwashed with a small amount of methylene chloride
  4. washThe filtrate was washed with sodium bicarbonate solution and water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customThe residue remaining was chromatographed on silica gel with hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-208d73f0b8844055a1674d9a49c5bc6b
출처 데이터셋
uspto-grants-1998_09
특허 번호
US05811548

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