Hydrochloric Acid → ((R)-2-carbamoyl-propyl)-carbamic acid tert-butyl ester

HRID 246125노트

반응식

HRID 246125 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C@@H:10]([CH3:14])[C:11](O)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N:16](C)CCCN=C=NCC.ON1C(=O)CCC1=O.[OH-].[NH4+].Cl>ClCCl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C@H:10]([C:11](=[O:12])[NH2:16])[CH3:14])([CH3:4])([CH3:3])[CH3:2]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 80170N-HydroxysuccinimideHCID 11041840(R)-3-((tert-butoxycarbonyl)amino)-2-methylpropanoic acid

생성물 1

HCID 22845901((R)-2-carbamoyl-propyl)-carbamic acid tert-butyl ester수율 72%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

(R)-3-(tert-Butoxycarbonylamino)-2-methylpropanoic acid (465 mg, 2.3 mmol) was dissolved in dichloromethane (11 ml). 4-Dimethylaminopyridine (280 mg, 2.3 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (877 mg, 4.58 mmol) were added, followed by N-hydroxysuccinimide (290 mg, 2.52 mmol). After 4 h of stirring at room temperature, concentrated ammonium hydroxide (1.6 ml) was added slowly. The reaction mixture was stirred for an additional 20 min then aqueous HCl and ethyl acetate were added and the aqueous layer was extracted six times with ethyl acetate. The combined organic layers were washed with sodium bicarbonate solution and dried over sodium sulfate. After evaporation, the residue was purified by silica gel chromatography to give 335 mg (72%) of ((R)-2-carbamoyl-propyl)-carbamic acid tert-butyl ester. (M+Na)+=225.

후처리

  1. stirringThe reaction mixture was stirred for an additional 20 min
  2. extractionthe aqueous layer was extracted six times with ethyl acetate
  3. washThe combined organic layers were washed with sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation
  6. customthe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-f28b6b3edde042c796bb9ce5b567ae25
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658646B2

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