Dichloromethane → glycyl-D-alanine benzyl ester hydrochloride

HRID 35712

반응식

HRID 35712 반응식
C(Cl)[Cl:2].C(OC([NH:11][CH2:12][C:13](O)=[O:14])=O)(C)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:27]([O:34][C:35](=[O:39])[C@@H:36]([CH3:38])[NH2:37])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(N(CC)CC)C>[ClH:2].[CH2:27]([O:34][C:35](=[O:39])[C@@H:36]([CH3:38])[NH:37][C:13](=[O:14])[CH2:12][NH2:11])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 2802425D-Alanine, phenylmethyl ester, 4-methylbenzenesulfonate (1:1)

생성물 1

HCID 67788730glycyl-D-alanine benzyl ester hydrochloride수율 70%

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

To a cold (0° C.) solution of 100 ml. methylene chloride containing 10 g. (57 mm) of N-t-butyloxycarbonylglycine, 20 g. (57 mm) of D-alanine benzyl ester p-toluenesulfonic acid salt and 5.77 g. (57 mm) of triethylamine was added 12.3 g. (60 mm) of dicyclohexylcarbodiimide and the resulting reaction mixture allowed to warm to room temperature. After 18 hours the mixture was filtered and the filtrate concentrated in vacuo. The residue was dissolved in 200 ml. of ethyl acetate and the organic layer washed with 2.5% hydrochloric acid, water, a saturated sodium bicarbonate solution and a brine solution. The organic layer was separated, dried over magnesium sulfate and evaporated under reduced pressure. To the resulting oil 200 ml. of dioxane saturated with hydrogen chloride was added. After 30 minutes 400 ml. of diethyl ether was added and the product filtered under nitrogen, 10.9 g. (70% yield).

후처리

  1. customTo a cold (0° C.) solution of 100 ml
  2. filtrationAfter 18 hours the mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. dissolutionThe residue was dissolved in 200 ml
  5. washof ethyl acetate and the organic layer washed with 2.5% hydrochloric acid, water
  6. customThe organic layer was separated
  7. dry with materialdried over magnesium sulfate
  8. customevaporated under reduced pressure
  9. additionof dioxane saturated with hydrogen chloride was added
  10. additionof diethyl ether was added
  11. filtrationthe product filtered under nitrogen

출처 및 근거

ORD 기록
ord-8bda6fe018d94c36b8bf2b8944589225
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04767743

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