Dicyclohexylcarbodiimide → ethyl-N-[(benzyloxy)carbonyl]-L-isoleucinate

HRID 346114

反応式

HRID 346114 の反応式
C1N(COCCO)[C:4]2N=C(N)N=C(O)[C:3]=2N=1.[C:17]([NH:27][C@H:28]([C:33]([OH:35])=[O:34])[C@H:29]([CH2:31][CH3:32])[CH3:30])([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH2:3]([O:34][C:33](=[O:35])[C@H:28]([C@H:29]([CH2:31][CH3:32])[CH3:30])[NH:27][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[CH3:4]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 2724772N-[(Phenylmethoxy)carbonyl]-L-isoleucine2 回HCID 178508933HCID 178508933、化合物

生成物 1

HCID 131717047ethyl-N-[(benzyloxy)carbonyl]-L-isoleucinate収率 61.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of acyclovir (1.0 g, 4.4. mmol; Burroughs Wellcome Co.), 4-dimethylaminopyridine (74 mg, 0.6 mmol; Aldrich Chemical Co. and Chem. Ber. 89 2921-33 [1956]), 1,3-dicyclohexylcarbodiimidide (1.6 g, 8.0 mmol; Aldrich Chemical Co. and U.S. Pat. No. 2,656,383), N-carbobenzoxy-L-isoleucine (1.8 g, 6.6 mmol; Sigma Chemical Co. and Bull. Chem. Soc. Jap (1966) 39 947 or Tetrahedron 40 (24) 5207-11 [1984]), and molecular sieves (0.3 g, Davison type 3A; Fisher Scientific, Co.) in dry N,N-dimethylformamide (80 ml) was stirred at room temperature under nitrogen. After 4 days, additional 1,3-dicyclohexylcarbodiimide (1.6 g, 8.0 mmol) and N-carbobenzoxy-L-isoleucine (1.8 g, 6.6 mmol) were added. Stirring at room temperature was continued for 7 days. The resulting mixture was filtered and the clear filtrate was concentrated in vacuo to a semi-solid residue. Elution of the residue from silica gel 60 (EM, 230-400 mesh; 8.5×14 cm) with 2.5-5% methanol/methylene chloride gave 2-[2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl-N-[(benzyloxy)carbonyl]-L-isoleucinate 0.8 g, 45%) as a white solid; mp 155°-157° C.

後処理

  1. waitwas continued for 7 days
  2. filtrationThe resulting mixture was filtered
  3. concentrationthe clear filtrate was concentrated in vacuo to a semi-solid residue
  4. washElution of the residue from silica gel 60 (EM, 230-400 mesh; 8.5×14 cm) with 2.5-5% methanol/methylene chloride

出典と根拠

ORDレコード
ord-dca97d3e18964b53a45edf7275e38ef7
出典データセット
uspto-grants-1991_10
特許番号
US05061708

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