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Diisopropylethylamine → tert-butyl 1-((2R)-3-(benzyloxy)-1-(2-methyl-1-oxo-4-phenyl-2,8-diazaspiro[4.6]undecan-8-yl)-1-oxopropan-2-ylamino)-2-methyl-1-oxopropan-2-ylcarbamate

HRID 1036709
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HRID 1036709 반응식
[CH3:1][N:2]1[CH2:6][CH:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]2([CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[C:3]1=[O:19].[CH2:20]([O:27][CH2:28][C@@H:29]([NH:33][C:34](=[O:46])[C:35]([NH:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])([CH3:37])[CH3:36])[C:30](O)=[O:31])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CCN(C(C)C)C(C)C.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CC#N.O>[CH2:20]([O:27][CH2:28][C@@H:29]([NH:33][C:34](=[O:46])[C:35]([NH:38][C:39](=[O:40])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:37])[CH3:36])[C:30]([N:15]1[CH2:16][CH2:17][CH2:18][C:4]2([C:3](=[O:19])[N:2]([CH3:1])[CH2:6][CH:5]2[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13][CH2:14]1)=[O:31])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 10894202(R)-3-(Benzyloxy)-2-(2-((tert-butoxycarbonyl)amino)-2-methylpropanamido)propanoic acid2회HCID 710605462-Methyl-4-phenyl-2,8-diazaspiro[4.6]undecan-1-one

생성물 1

HCID 71060614
tert-butyl 1-((2R)-3-(benzyloxy)-1-(2-methyl-1-oxo-4-phenyl-2,8-diazaspiro[4.6]undecan-8-yl)-1-oxopropan-2-ylamino)-2-methyl-1-oxopropan-2-ylcarbamate

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

A diastereomeric mixture. of 2-methyl-4-phenyl-2,8-diazaspiro[4.6]undecan-1-one (200 mg; 0.774 mmol) in MeCN (2.58 ml) was treated with (R)-3-(benzyloxy)-2-(2-(tert-butoxy carbonylamino)-2-methyl propanamido) propanoic acid (Intermediate 3A) (295 mg; 0.774 mmol) followed by DIPEA (541 ul; 3.10 mmol). After stirring for 5 minutes, ®T3P (amide coupling agent 50% in DMF, 904 ul, 1.548 mmol) was added and the mixture was stirred at RT overnight. The resulting mixture was diluted with water and extracted with EtOAc. The combined organic extracts were dried (MgSO4) and concentrated in vacuo. Purification by chromatography on silica eluting with 50-100% EtOAc in iso-hexane afforded the title compound;

후처리

  1. stirringthe mixture was stirred at RT overnight
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by chromatography on silica eluting with 50-100% EtOAc in iso-hexane

출처 및 근거

ORD 기록
ord-0ba357c198de47f0b69f9f56ccf0d56e
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08546416B2

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