Dicyclohexylcarbodiimide → HCID 53875478, 화합물

HRID 65596노트

반응식

HRID 65596 반응식
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:15]([NH:17][C@H:18]([C:27]([OH:29])=O)[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)=[O:16])[CH2:13][OH:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ON1C(=O)CCC1=O.Cl.[CH2:39]([O:41][C:42](=[O:45])[CH2:43][NH2:44])[CH3:40].C1(N=C=NC2CCCCC2)CCCCC1>C(N(CC)CC)C.CN(C)C=O>[CH2:39]([O:41][C:42](=[O:45])[CH2:43][NH:44][C:27](=[O:29])[C@H:18]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=1)[NH:17][C:15](=[O:16])[C@H:12]([CH2:13][OH: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])[CH3:40]

참가 물질

7

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 2723640Glycine ethyl ester, hydrochlorideHCID 53862480(S)-2-((S)-2-(((Benzyloxy)carbonyl)amino)-3-hydroxypropanamido)-3-(4-hydroxyphenyl)propanoic acid

생성물 1

HCID 53875478HCID 53875478, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

To a stirred mixture consisting of 4.82 g. of N-benzyloxycarbonyl-L-seryl-L-tyrosine, 1.519 g. of N-hydroxysuccinimide, 1.675 g. of glycine ethyl ester hydrochloride, and 60 ml. of N,N-dimethylformamide, cooled to -15° C., is added first 1.68 ml. of triethylamine and then 2.48 g. of dicyclohexylcarbodiimide, and the resulting mixture is stirred at -15° C. for 2 hours and at room temperature for 25 hours. The mixture is then concentrated to remove solvent, and the residue is partitioned between dilute hydrochloric acid and ethyl acetate. The organic layer is separated, washed with saturated aqueous sodium chloride, with saturated aqueous sodium bicarbonate, and with saturated aqueous sodium chloride again, dried, and evaporated to give a solid residue of N-benzyloxycarbonyl-L-seryl-L-tyrosylglycine ethyl ester; m.p. 166°-169° C., following crystallization from ethyl acetate; [α]D25 -23.2° (2% in methanol).

후처리

  1. additionis added first 1.68 ml
  2. concentrationThe mixture is then concentrated
  3. customto remove solvent
  4. customthe residue is partitioned between dilute hydrochloric acid and ethyl acetate
  5. customThe organic layer is separated
  6. washwashed with saturated aqueous sodium chloride, with saturated aqueous sodium bicarbonate
  7. dry with materialwith saturated aqueous sodium chloride again, dried
  8. customevaporated

출처 및 근거

ORD 기록
ord-c2d86e636e8d455ea106eba45183fb99
출처 데이터셋
uspto-grants-1978_12
특허 번호
US04128540

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