4-Methylmorpholine → carbobenzoxy-beta-alanyl-L-proline t-butyl ester

HRID 27347

反応式

HRID 27347 の反応式
[C:1]([NH:11][CH2:12][CH2:13][C:14]([OH:16])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CN1CCOCC1.C(OC(Cl)=O)C(C)C.Cl.[C:33]([O:37][C:38](=[O:44])[C@@H:39]1[CH2:43][CH2:42][CH2:41][NH:40]1)([CH3:36])([CH3:35])[CH3:34]>C(N(CC)CC)C.CN(C)C=O.O1CCCC1>[C:33]([O:37][C:38](=[O:44])[C@@H:39]1[CH2:43][CH2:42][CH2:41][N:40]1[C:14](=[O:16])[CH2:13][CH2:12][NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])([CH3:36])([CH3:34])[CH3:35]

参加物

8

反応物 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 75313N-Benzyloxycarbonyl-beta-alanineHCID 6453107tert-Butyl L-prolinate hydrochloride

生成物 1

HCID 54135485carbobenzoxy-beta-alanyl-L-proline t-butyl ester

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

4.46 g. of carbobenzoxy-β-alanine is dissolved in 20 ml. of tetrahydrofuran and the resulting solution cooled to -10° C. With constant stirring of the solution, 2.4 ml. of N-methylmorpholine followed by 2.6 ml. of isobutylchloroformate are added and the resulting reaction mixture is stirred thereafter for approximately 5 minutes at -10° C. 4.16 g. of L-proline t-butyl ester hydrochloride in 20 ml. of dimethylformamide and 2.8 ml. of triethylamine is added to the reaction mixture which is thereafter stirred overnight, while slowly warming to room temperature. The solvent of the reaction mixture is evaporated in vacuo at 30°-35°. The residue is dissolved in 800 ml. of ethyl acetate which is washed with (2×150 ml.) a 10% citric acid solution, with (1×150 ml.) water, with (2×150 ml.) saturated solution of sodium bicarbonate and then with (2×100 ml.) water. The organic layer is dried with anhydrous magnesium sulfate and the solvent evaporated to yield carbobenzoxy-β-alanyl-L-proline t-butyl ester.

後処理

  1. customthe resulting reaction mixture
  2. stirringis stirred
  3. stirringis thereafter stirred overnight
  4. customThe solvent of the reaction mixture is evaporated in vacuo at 30°-35°
  5. dissolutionThe residue is dissolved in 800 ml
  6. washof ethyl acetate which is washed with (2×150 ml.) a 10% citric acid solution
  7. dry with materialThe organic layer is dried with anhydrous magnesium sulfate
  8. customthe solvent evaporated

出典と根拠

ORDレコード
ord-c7cd6af73aca49feafad7a587907044d
出典データセット
uspto-grants-1980_09
特許番号
US04221706

関連ノート

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