Dicyclohexylcarbodiimide → HCID 53875478、化合物

HRID 65596ノート

反応式

HRID 65596 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 53875478HCID 53875478、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c2d86e636e8d455ea106eba45183fb99
出典データセット
uspto-grants-1978_12
特許番号
US04128540

反応ノート

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