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Hydrochloric Acid → (2R,5S)-2-Hydroxymethyl-5-(3-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester

HRID 1527347
ノート
印刷プレビュー

反応式

HRID 1527347 の反応式
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([C@@H:13]2[CH2:17][CH2:16][C@H:15]([CH2:18][OH:19])[NH:14]2)=[O:12])[CH:7]=[CH:8][CH:9]=1.CCN(CC)CC.[CH2:29]([O:36][C:37](Cl)=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.Cl>C(Cl)Cl>[CH2:29]([O:36][C:37]([N:14]1[C@H:13]([C:11](=[O:12])[NH:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:20])([F:1])[F:21])[CH:5]=2)[CH2:17][CH2:16][C@@H:15]1[CH2:18][OH:19])=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 71042622(2S,5R)-5-Hydroxymethyl-pyrrolidine-2-carboxylic acid (3-trifluoromethoxy-phenyl)-amide

生成物 1

HCID 68284198(2R,5S)-2-Hydroxymethyl-5-(3-trifluoromethoxy-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
2 回

実験手順

To a solution of (2S,5R)-5-hydroxymethyl-pyrrolidine-2-carboxylic acid (3-trifluoromethoxy-phenyl)-amide (797 mg, 2.62 mmol) (prepared as described in Scheme B3) in CH2Cl2 (10 mL) was added under nitrogen atmosphere Et3N (440 μl, 3.14 mmol) and benzylchloroformate (406 μl, 2.88 mmol) and the mixture was further stirred at RT overnight. CH2Cl2 and HCl 0.1N were added, the layers were separated and the aqueous one re-extracted with CH2Cl2. The crude organic extracts were washed with brine dried over Na2SO4, filtered and concentrated. The crude material was purified by flash column chromatography on silica gel (c-hexane/EtOAc gradient 100:0 to 1:1) to give the title compound. MS (LC-MS): 439 [M+H]+; tR (HPLC conditions b) 4.88 min.

後処理

  1. customthe layers were separated
  2. extractionthe aqueous one re-extracted with CH2Cl2
  3. washThe crude organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by flash column chromatography on silica gel (c-hexane/EtOAc gradient 100:0 to 1:1)

出典と根拠

ORDレコード
ord-826c15bd0185463680cfaaf822286702
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09085555B2

反応ノート

読み込み中…

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