Dicyclohexylcarbodiimide → CARBOBENZYLOXY-L-ISOLEUCYL-L-TRYPTOPHAN METHYL ESTER

HRID 2083842ノート

反応式

HRID 2083842 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:17]([OH:19])=O)[C@H:13]([CH2:15][CH3:16])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:21][O:22][C:23](=[O:36])[C@H:24]([CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1)[NH2:25].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>CO.C(N(CC)CC)C.CN(C)C=O>[CH3:21][O:22][C:23](=[O:36])[C@H:24]([CH2:26][C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH:29][CH:28]=1)[NH:25][C:17](=[O:19])[C@H:12]([C@H:13]([CH2:15][CH3:16])[CH3:14])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

参加物

8

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 2724772N-[(Phenylmethoxy)carbonyl]-L-isoleucineHCID 2734891Methyl tryptophanate hydrochloride

生成物 1

HCID 21074402CARBOBENZYLOXY-L-ISOLEUCYL-L-TRYPTOPHAN METHYL ESTER

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

Nα -Benzyloxycarbonyl-L-isoleucine, 2.65 g., and 2.54 g. of L-tryptophan methyl ester hydrochloride are dissolved in 30 ml. of dimethylformamide and cooled in an ice bath. Triethylamine, 1.4 ml., is added and then 1.5 g. of 1-hydroxy-benzotriazole. Lastly 2.3 g. of dicyclohexylcarbodiimide is added and the reaction let warm to room temperature with stirring continued for 40 hours. The mixture is filtered and the solvent evaporated. The residue is dissolved in 150 ml. of ethyl acetate and washed with 0.5 N hydrochloric acid, saturated sodium chloride solution, 5% sodium bicarbonate solution and finally with saturated sodium chloride solution. The ethyl acetate solution is dried over magnesium sulfate, filtered and the solution evaporated. The product is crystallized from methanol-ether-hexane to give 2.58 g. of the above named product, mp. 152°-155° C; [α]D23 -16.6° (c 1.95, methanol).

後処理

  1. addition, is added
  2. filtrationThe mixture is filtered
  3. customthe solvent evaporated
  4. dissolutionThe residue is dissolved in 150 ml
  5. washof ethyl acetate and washed with 0.5 N hydrochloric acid, saturated sodium chloride solution, 5% sodium bicarbonate solution and finally with saturated sodium chloride solution
  6. dry with materialThe ethyl acetate solution is dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solution evaporated
  9. customThe product is crystallized from methanol-ether-hexane
  10. customto give 2.58 g

出典と根拠

ORDレコード
ord-aecfb805071744e5a65d5108de7461b4
出典データセット
uspto-grants-1978_04
特許番号
US04086219

反応ノート

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