4-Methylmorpholine → H-Gly-Asp(OBzl)-Val-OBzl

HRID 1376687ノート

反応式

HRID 1376687 の反応式
[NH2:1][C@H:2]([C:14]([NH:16][C@H:17]([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[CH:18]([CH3:20])[CH3:19])=[O:15])[CH2:3][C:4](=[O:13])[O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.FC(C(O)=O)(F)F.[NH:38](C(OC(C)(C)C)=O)[CH2:39][C:40](ON1C(=O)CCC1=O)=[O:41].CN1CCOCC1>C(OCC)(=O)C>[NH2:38][CH2:39][C:40]([NH:1][C@H:2]([C:14]([NH:16][C@H:17]([C:21]([O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:22])[CH:18]([CH3:20])[CH3:19])=[O:15])[CH2:3][C:4](=[O:13])[O:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:41]

参加物

5

反応物 3

HCID 79724-MethylmorpholineHCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide esterHCID 131720167H-Asp(OBzl)-Val-OBzl.TFA

生成物 1

HCID 131720165H-Gly-Asp(OBzl)-Val-OBzl

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
20 °C

実験手順

A solution of 4.2 g. of H-Asp(OBzl)-Val-OBzl.TFA in 50 ml of ethyl acetate is treated in succession with 2.72 g of Boc-Gly-OSu and 0.88 ml of N-methylmorpholine and then stirred at 20° C. for 72 hours. The reaction mixture is partitioned between ethyl acetate and water and the organic phase is washed with 5% KHSO4 /10% K2SO4 solution, water, saturated NaHCO3 solution, water and saturated NaCl solution. After drying the solution is concentrated. The residue is dissolved in 30 ml of trifluoroacetic acid held at 20° C. for 20 minutes and then concentrated. After crystallization from ethyl acetate/hexane there are obtained 3.5 g of H-Gly-Asp(OBzl)-Val-OBzl, TFA (1:1), m.p. 150°-151° C.

後処理

  1. customThe reaction mixture is partitioned between ethyl acetate and water
  2. washthe organic phase is washed with 5% KHSO4 /10% K2SO4 solution, water, saturated NaHCO3 solution, water and saturated NaCl solution
  3. customAfter drying the solution
  4. concentrationis concentrated
  5. dissolutionThe residue is dissolved in 30 ml of trifluoroacetic acid
  6. waitheld at 20° C. for 20 minutes
  7. concentrationconcentrated
  8. customAfter crystallization from ethyl acetate/hexane there

出典と根拠

ORDレコード
ord-0619bf1890e8441487c3a96f4ce9cd74
出典データセット
uspto-grants-1997_09
特許番号
US05663297

反応ノート

読み込み中…