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Dicyclohexylcarbodiimide → (S)-Phenylmethyl 2-[[1-[[[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]carbonyl]-3-methylbutoxy]methyl]-1-pyrrolidinecarboxylate

HRID 1982641
ノート
印刷プレビュー

反応式

HRID 1982641 の反応式
[C:1]1([CH2:7][O:8][C:9]([N:11]2[CH2:15][CH2:14][CH2:13][C@H:12]2[CH2:16][O:17][CH:18]([C:23]([OH:25])=O)[CH2:19][CH:20]([CH3:22])[CH3:21])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:26][C@H:27]([C:32]([O-:34])=[O:33])C(C)(C)C.ON1C2C=C[CH:43]=[CH:44][C:39]=2N=N1.[CH:45]1(N=C=NC2CCCCC2)CCCCC1>ClCCl.CO>[CH3:45][C:44]([CH3:43])([O:34][C:32](=[O:33])[CH2:27][NH:26][C:23]([CH:18]([O:17][CH2:16][C@@H:12]1[CH2:13][CH2:14][CH2:15][N:11]1[C:9]([O:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:10])[CH2:19][CH:20]([CH3:21])[CH3:22])=[O:25])[CH3:39]
参加物反応条件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 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 57212195(2S)-phenylmethyl 2-[(1-carboxy-3-methylbutoxy)methyl]-1-pyrrolidinecarboxylateHCID 77068310tert-Butylglycinate

生成物 1

HCID 70468867(S)-Phenylmethyl 2-[[1-[[[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]carbonyl]-3-methylbutoxy]methyl]-1-pyrrolidinecarboxylate

試薬・触媒・溶媒

2
HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

(2S)-Phenylmethyl-2-[(1-carboxy-3-methylbutoxy)methyl]-1-pyrrolidinecarboxylate (center on side chain is R,S mixture), 2 g (0.0057 mol), is dissolved in 100 ml of dichloromethane, cooled to 0° C. and 1.1 g (0.0084 mol) of t-butylglycinate, 0.88 g (0.0057 mol) of 1-hydroxybenzotriazole and 1.32 g (0.0064 mol) of dicyclohexylcarbodiimide are added. The mixture is allowed to reach room temperature and stirred 14 hours, filtered, the solvent evaporated in vacuo and the residue dissolved in 200 ml of dichloromethane and washed successively with a 5% aqueous solution of sodium chloride, 2×200 ml. The dichloromethane layer is separated, dried over sodium sulfate, evaporated in vacuo and the residue purified by chromatography using silica gel and eluting with dichloromethane-methanol (98:2) to give (S)-phenylmethyl 2-[[1-[[[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]carbonyl]-3-methoxy-butoxy]methyl]-1-pyrrolidinecarboxylate (2-position of pentane chain is R S), 1.75 g; [ α]D25 -70.2° (c 0.39, methanol).

後処理

  1. customto reach room temperature
  2. filtrationfiltered
  3. customthe solvent evaporated in vacuo
  4. dissolutionthe residue dissolved in 200 ml of dichloromethane
  5. washwashed successively with a 5% aqueous solution of sodium chloride, 2×200 ml
  6. customThe dichloromethane layer is separated
  7. dry with materialdried over sodium sulfate
  8. customevaporated in vacuo
  9. customthe residue purified by chromatography
  10. washeluting with dichloromethane-methanol (98:2)
  11. customto give (S)-phenylmethyl 2-[[1-[[[2-(1,1-dimethylethoxy)-2-oxoethyl]amino]carbonyl]-3-methoxy-butoxy]methyl]-1-pyrrolidinecarboxylate (2-position of pentane chain is R S), 1.75 g

出典と根拠

ORDレコード
ord-4f3a0b13dad54182bff78691e37f34ac
出典データセット
uspto-grants-1986_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04596819

反応ノート

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