Hydrogen Bromide → 1-[2(R)-[1(R)-carboxy-2-(3,4,4-trimethyl-2,5-dioxo-1-imidazolidinyl)ethyl]-3-cyclopentylpropionyl)piperdine

HRID 618473

反応式

HRID 618473 の反応式
C([O:5][C:6]([C@@H:8]([C@@H:20]([CH2:29][CH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)[C:21]([N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:22])[CH2:9][N:10]1[C:14](=[O:15])[C:13]([CH3:17])([CH3:16])[N:12]([CH3:18])[C:11]1=[O:19])=[O:7])(C)(C)C.Br>C(O)(=O)C.C(Cl)Cl>[C:6]([C@H:8]([C@@H:20]([CH2:29][CH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)[C:21]([N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:22])[CH2:9][N:10]1[C:14](=[O:15])[C:13]([CH3:17])([CH3:16])[N:12]([CH3:18])[C:11]1=[O:19])([OH:7])=[O:5]

参加物

5

反応物 2

HCID 260Hydrogen BromideHCID 233822641-[2(R)-[1(S)-(tert-butoxycarbonyl)-2-(3,4,4-trimethyl-2,5-dioxo-1imidazolidinyl)ethyl]-3-cyclopentylpropionyl]piperidine

生成物 1

HCID 112701291-[2(R)-[1(R)-carboxy-2-(3,4,4-trimethyl-2,5-dioxo-1-imidazolidinyl)ethyl]-3-cyclopentylpropionyl)piperdine

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

A solution of 15.11 g of the 9:1 mixture from Example 4 in 15 ml of acetic acid was treated at 0° with 15 ml of 33% hydrogen bromide in acetic acid and stirred at 0° for 4 hrs. The solution was diluted with methylene chloride, washed with water and the organic phase was dried, filtered and evaporated. The residue was crystallized from 26 ml of tert-butyl methyl ether and 26 ml of hexane, after which 6.90 g (70%) of diastereomer-pure (de>98%) 1-[2(R)-[1(R)-carboxy-2-(3,4,4-trimethyl-2,5-dioxo-1-imidazolidinyl)ethyl]-3-cyclopentylpropionyl]piperidine (IX), m.p. 111-114°, was obtained. IR (KBr): 1770m and 1715s (C=O).

後処理

  1. washwashed with water
  2. customthe organic phase was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was crystallized from 26 ml of tert-butyl methyl ether and 26 ml of hexane

出典と根拠

ORDレコード
ord-d0835afafe8540c1bf49d6379262a5f3
出典データセット
uspto-grants-1999_09
特許番号
US05952507

関連ノート

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