Boc-L-Valine → HCID 178448372, 화합물

HRID 552080

반응식

HRID 552080 반응식
[CH3:1][CH:2]([C@H:4]([NH2:23])C([O:7][CH2:8][CH2:9][O:10][CH2:11][N:12]1[C:16]2[NH:17][C:18]([NH2:22])=[N:19][C:20](=[O:21])[C:15]=2[N:14]=[CH:13]1)=O)[CH3:3].[NH:24]([C:32]([O:34]C(C)(C)C)=O)[C@H:25]([C:29]([OH:31])=[O:30])[CH:26]([CH3:28])[CH3:27]>C(N(CC)CC)C>[CH:13]1[N:12]([CH2:11][O:10][CH2:9][CH2:8][OH:7])[C:16]2[N:17]=[C:18]([NH2:22])[N:19]=[C:20]([OH:21])[C:15]=2[N:14]=1.[CH3:1][CH:2]([C@H:4]([NH2:23])[C:32]([NH:24][C@H:25]([C:29]([OH:31])=[O:30])[CH:26]([CH3:27])[CH3:28])=[O:34])[CH3:3]

참가 물질

4

반응물 2

HCID 83693Boc-L-ValineHCID 178448382HCID 178448382, 화합물

생성물 1

HCID 178448372HCID 178448372, 화합물

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

A mixture of the desired stereoisomeric form of Boc-Val, and dicyclohexyl carbodiimide (DCC), in dimethylformamide (DMF) in a ratio of 1:2 DCC/Boc-Val was stirred for 1 hr at 0° C. under nitrogen atmosphere. A solution of acyclovir (1) and 4-N,N(dimethylamino) pyridine (DMAP) was added to the reaction mixture, stirred for 18 hrs and then filtered. The solvent of the filtrate was partially removed in vacuo and the impure solution was added dropwise to cold diethyl ether. The resulting precipitate (2) was filtered and dried, followed by acidolytic removal (treating Boc-Val-ACV with trifluoroacetic acid (TFA) for 30 min at 0° C.) of the Boc protecting group to yield Val-ACV (3). Compound (3) was neutralized by triethylamine (TEA) and treated with the amino acid anhydride of Boc-Val for about hrs. The solvent was removed from the reaction mixture in vacuo and the reaction mixture was added dropwise to the cold diethyl ether. The resulting precipitate (4) was filtered, dried and the Boc group was deprotected (acidolytic removal) to yield the desired dipeptide ester of acyclovir Val-Val-ACV (5).

후처리

  1. customThe solvent was removed from the reaction mixture in vacuo
  2. additionthe reaction mixture was added dropwise to the cold diethyl ether
  3. filtrationThe resulting precipitate (4) was filtered
  4. customdried
  5. custom(acidolytic removal)

출처 및 근거

ORD 기록
ord-3ad61183081449489f1338872da22f62
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951774B2

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