Hydroxypyridinone → Fmoc-D-Hyp-Gly-OtBu

HRID 374370

반응식

HRID 374370 반응식
[N:1]1([C:10]([O:12][CH2:13][CH:14]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:11])[CH2:9][C@@H:7]([OH:8])[CH2:6][C@@H:2]1[C:3](O)=[O:4].[NH2:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].ON1C=CC=CC1=O.F[B-](F)(F)F.C(C(=NOC(N(C)C)=[N+](C)C)C(OCC)=O)#N.C(N(C(C)C)CC)(C)C>C(#N)C.CN(C=O)C>[N:1]1([C:10]([O:12][CH2:13][CH:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21]3[C:26]2=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:11])[CH2:9][C@@H:7]([OH:8])[CH2:6][C@@H:2]1[C:3]([NH:27][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:4]

참가 물질

8

반응물 5

HCID 69975HydroxypyridinoneHCID 81531DiisopropylethylamineHCID 151417Glycine tert-butyl esterHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 7408199(2R,4S)-1-(((9H-Fluoren-9-yl)methoxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

생성물 1

HCID 131717656Fmoc-D-Hyp-Gly-OtBu

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

실험 절차

1.4 g of Fmoc-D-Hyp-OH are dissolved in 25 ml of dry acetonitrile and then 1.05 g of H-Gly-OtBu and 0.445 g of N-hydroxypyridone are added. Then 1.31 g of O-[(cyano(ethoxycarbonyl)methylidene)amino]-1,1,3,3-tetramethyluronium tetrafluoroborate (TOTU) are introduced in/portions within 10 minutes, as well as 1.03 ml of diisopropylethylamine in 15 ml of DMF dropwise over the course of 15 minutes. After 1 h, the mixture is concentrated, the residue is taken up in ethyl acetate and extraction with sodium chloride solution is carried out. The organic phase is dried over sodium sulfate and evaporated to dryness. The remaining oil is taken up in a little ether and added dropwise to petroleum ether while stirring. The flocculent precipitate is filtered off with suction and dried in vacuo.

후처리

  1. customdropwise over the course of 15 minutes
  2. concentrationthe mixture is concentrated
  3. extractionextraction with sodium chloride solution
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customevaporated to dryness
  6. additionadded dropwise to petroleum ether
  7. filtrationThe flocculent precipitate is filtered off with suction
  8. customdried in vacuo

출처 및 근거

ORD 기록
ord-1c72ccf168904bfabd7b4c73a04aa3e8
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05166394

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