tert-Butyl methyl ether → Methyl 2-{3-[2-(4-bromophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyloxymethyl}-6-methylbenzoate

HRID 748013

반응식

HRID 748013 반응식
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([CH3:17])=[C:13]([CH2:15]I)[N:14]=2)=[CH:6][CH:5]=1.[OH:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH:21]([O:25][CH2:26][C:27]2[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[C:28]=2[C:29]([O:31][CH3:32])=[O:30])[CH2:20]1.C(OC)(C)(C)C>CN(C)C=O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([CH3:17])=[C:13]([CH2:15][O:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH:21]([O:25][CH2:26][C:27]4[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[C:28]=4[C:29]([O:31][CH3:32])=[O:30])[CH2:20]3)[N:14]=2)=[CH:6][CH:5]=1

참가 물질

6

반응물 4

HCID 15413tert-Butyl methyl etherHCID 24758Sodium hydrideHCID 21980299Methyl 2-(3-hydroxycyclohexyloxymethyl)-6-methylbenzoateHCID 224936662-(4-Bromophenyl)4-iodomethyl-5-methyloxazole

생성물 1

HCID 22493646Methyl 2-{3-[2-(4-bromophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyloxymethyl}-6-methylbenzoate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

At room temperature, 50 mg of a 60% sodium hydride suspension and then 408 mg of 2-(4-bromophenyl)-4-iodomethyl-5-methyloxazole were added to a solution of 200 mg of methyl 2-(3-hydroxycyclohexyloxymethyl)-6-methylbenzoate in 5 ml of dimethylformamide. After one hour, methyl tert-butyl ether was added, and the mixture was extracted with water. The organic phase was dried over magnesium sulfate, the solvents were removed under reduced pressure and the residue was purified by RP-HPLC. This gave 49 as a light-yellow oil. C27H30BrNO5 (528.45), MS(ESI): 528.2, 530.2 (M+H+).

후처리

  1. extractionthe mixture was extracted with water
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customthe solvents were removed under reduced pressure
  4. customthe residue was purified by RP-HPLC

출처 및 근거

ORD 기록
ord-35e920e9d42e4192b9e0e2f316c1c05a
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07399777B2

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