Potassium Carbonate → {4-[4-(2-{Benzyl-[2-(4-benzyloxy-3-formylaminophenyl)-2-(R)-hydroxyethyl]amino}-ethoxy)phenyl]butyl}carbamic acid benzyl ester

HRID 1696831노트

반응식

HRID 1696831 반응식
[CH2:1]([O:8][C:9](=[O:32])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:33]([O:40][C:41]1[CH:46]=[CH:45][C:44]([C@@H:47]([OH:50])[CH2:48]Br)=[CH:43][C:42]=1[NH:51][CH:52]=[O:53])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C([O-])([O-])=O.[K+].[K+]>O1CCCC1>[CH2:1]([O:8][C:9](=[O:32])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH2:23][N:24]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:48][C@@H:47]([C:44]2[CH:45]=[CH:46][C:41]([O:40][CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[C:42]([NH:51][CH:52]=[O:53])[CH:43]=2)[OH:50])=[CH:19][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 11142645(R)-N-[5-(2-Bromo-1-hydroxyethyl)-2-(phenylmethoxy)phenyl]formamideHCID 58100148{4-[4-(2-Benzylaminoethoxy)phenyl]butyl}carbamic acid benzyl ester

생성물 1

HCID 58100114{4-[4-(2-{Benzyl-[2-(4-benzyloxy-3-formylaminophenyl)-2-(R)-hydroxyethyl]amino}-ethoxy)phenyl]butyl}carbamic acid benzyl ester수율 50.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Benzylamine 16 (619 mg, 1.43 mmol) was added to a suspension of bromoalcohol 5 (500 mg, 1.43 mmol) and K2CO3 (495 mg, 3.58 mmol) methanol (10 mL) and tetrahydrofuran (5 mL). The suspension was stirred at ambient temperature for 15 h, then heated to 55° C. for 75 h. The solid was vacuum filtered and the filtrate was concentrated under vacuum. The resulting oil was subjected to column chromatography eluting with 5-50% ethyl acetate in hexanes to afford the desired product 17 (508 mg, 5%) as an off-white solid: 1H NMR (500 MHz, CDCl3) δ 1.45-1.62 (m, 4H), 2.54 (t, 2H), 2.65-2.71 (m, 1H), 3.14-3.23 (m, 3H), 3.58-3.74 (m, 1H), 3.88-4.09 (m, 3H), 4.71 (br, 2H), 5.04-5.21 (m, 4H), 6.79-7.25 (m, 6H), 7.34-7.52 (m, 16H), 7.65-7.87 (m, 1H), 8.32-8.49 (m, 1H); m/z, (ESI) 702 [C43H47N3O6+H]+.

후처리

  1. temperatureheated to 55° C. for 75 h
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated under vacuum
  4. washeluting with 5-50% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-1636d5e5f75a4ebf8019bf4e16a1255f
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163758B2

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