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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
ノート
印刷プレビュー

反応式

HRID 1036709 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 10894202(R)-3-(Benzyloxy)-2-(2-((tert-butoxycarbonyl)amino)-2-methylpropanamido)propanoic acid2 回HCID 710605462-Methyl-4-phenyl-2,8-diazaspiro[4.6]undecan-1-one

生成物 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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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;

後処理

  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

出典と根拠

ORDレコード
ord-0ba357c198de47f0b69f9f56ccf0d56e
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08546416B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート