4-Methylmorpholine → Benzyl (tert-butoxycarbonyl)glycylglycinate

HRID 1086785

反応式

HRID 1086785 の反応式
[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([OH:5])=O.CCN=C=NCCCN(C)C.[NH2:24][CH2:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27].S(C1C=CC(C)=CC=1)([O-])(=O)=O.CN1CCOCC1>C(Cl)(Cl)Cl.C(#N)C>[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([NH:24][CH2:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=[O:5]

参加物

8

反応物 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 85570p-ToluenesulfonateHCID 409140Benzyl glycinate

生成物 1

HCID 3244524Benzyl (tert-butoxycarbonyl)glycylglycinate収率 93.7%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒2 回HCID 6342Acetonitrile溶媒

反応条件

温度
-15 °C

実験手順

Boc-Gly-OH (17.52 g, 0.1 mole) in a mixture of CHCl3 (50 ml) and acetonitrile (50 ml) was cooled to -15° C. and EDCI (19.17 g, 0.1 mole) was added and stirred for 20 minutes. To this, a pre-cooled solution of H-Gly-OBzl.tosylate (37.1 g, 0.11 mole), NMM (12.09 ml, 0.11 mole) in CHCl3 (100 ml) was added and stirred overnight at room temperature. After removing the solvent, the residue was taken in CHCl3 and extracted with acid and base. Chloroform was removed under reduced pressure, triturated with pet. ether, filtered, washed with pet. ether and dried to obtain 30.2 g of I (yield: 93.7%), m.p. 82°-83° C. Rf2, 0.52; Rf4, 0.82. Anal. Calcd. for C16H22N2O5 : C, 59.61; H, 6.88; N, 8.69%. Found C, 59.43; H, 6.88; N, 8.35%

後処理

  1. stirringstirred overnight at room temperature
  2. customAfter removing the solvent
  3. extractionextracted with acid and base
  4. customChloroform was removed under reduced pressure
  5. customtriturated with pet. ether
  6. filtrationfiltered
  7. washwashed with pet. ether
  8. customdried

出典と根拠

ORDレコード
ord-f3d2146e602044d387d3409607c9d625
出典データセット
uspto-grants-1991_07
特許番号
US05032271

関連ノート

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