Dichloromethane → (S)-3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-1,2,3,5,7,8-hexahydro-4-oxa-1,6-diaza-anthracene-6,7-dicarboxylic acid 6-tert-butyl ester 7-methyl ester

HRID 391864노트

반응식

HRID 391864 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:16])[CH:14]=O)=[CH:9][CH:8]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:35][O:36][C:37]([C@@H:39]1[CH2:48][C:47]2[C:42](=[CH:43][C:44](O)=[C:45]([NH2:49])[CH:46]=2)[CH2:41][N:40]1[C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])=[O:38].C(Cl)Cl>ClCCCl.O>[CH3:35][O:36][C:37]([CH:39]1[CH2:48][C:47]2[CH:46]=[C:45]3[C:44]([O:16][C@@H:13]([C:10]4[CH:9]=[CH:8][C:7]([O:6][CH2:5][C:4]5[CH:17]=[CH:18][C:19]([Cl:20])=[C:2]([Cl:1])[CH:3]=5)=[CH:12][CH:11]=4)[CH2:14][NH:49]3)=[CH:43][C:42]=2[CH2:41][N:40]1[C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])=[O:38]

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 5049666Sodium triacetoxyborohydrideHCID 59337426(S)-6-amino-7-hydroxy-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl esterHCID 86654900[4-(3,4-Dichloro-benzyloxy)-phenyl]-oxo-acetaldehyde

생성물 1

HCID 66719396(S)-3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-1,2,3,5,7,8-hexahydro-4-oxa-1,6-diaza-anthracene-6,7-dicarboxylic acid 6-tert-butyl ester 7-methyl ester수율 71.6%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 962Water용매

실험 절차

[4-(3,4-Dichloro-benzyloxy)-phenyl]-oxo-acetaldehyde (616 mg) was dissolved in DCE (25 mL) and sodium triacetoxyborohydride (520 mg) and (S)-6-Amino-7-hydroxy-3,4-dihydro-1H-isoquinoline-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester (644 mg) The mixture was stirred overnight at room temperature. DCM (50 mL) was added to the reaction mixture and poured into water (25 mL). The organic layer was washed with 10% Na2CO3 solution and brine, and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by flash chromatography (hexanes/ethyl acetate from 90:10 to 70:30) to give (S)-3-[4-(3,4-Dichloro-benzyloxy)-phenyl]-1,2,3,5,7,8-hexahydro-4-oxa-1,6-diaza-anthracene-6,7-dicarboxylic acid 6-tert-butyl ester 7-methyl ester (855 mg).

후처리

  1. washThe organic layer was washed with 10% Na2CO3 solution and brine
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue purified by flash chromatography (hexanes/ethyl acetate from 90:10 to 70:30)

출처 및 근거

ORD 기록
ord-926b538ae2c2443d88ecdc6a20796f16
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383644B2

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