Hydrochloric Acid → (S)-2-(tert-butoxycarbonylamino)-3-(4-chlorobutanamido)propanoic acid

HRID 58824노트

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HRID 58824 반응식
[Cl:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[NH:8]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:9]([C:12]([OH:14])=[O:13])[CH2:10][NH2:11].Cl>O1CCOCC1.C([O-])([O-])=O.[Na+].[Na+]>[C:18]([O:17][C:15]([NH:8][C@@H:9]([CH2:10][NH:11][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][Cl:1])[C:12]([OH:14])=[O:13])=[O:16])([CH3:21])([CH3:20])[CH3:19]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 783704-Chlorobutyryl chlorideHCID 2755946Boc-Dap-OH

생성물 1

HCID 117607805(S)-2-(tert-butoxycarbonylamino)-3-(4-chlorobutanamido)propanoic acid수율 64.4%

시약·촉매·용매 2

HCID 10340Sodium Carbonate용매HCID 312751,4-Dioxane용매

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온도
0 °C

실험 절차

4-Chlorobutanoyl chloride (12.1 g, 86 mmol) was added to a solution of Boc-L-Dap (16.0 g, 78 mmol) in dioxane (160 mL) and 10% aqueous Na2CO3 (180 mL) at 0° C. dropwise. The reaction mixture was stirred at 0° C. for 1 h and then allowed to warm to ambient temperature and stirred overnight. The mixture was acidified with 1N aqueous hydrochloric acid to pH=3 and extracted with EtOAc (300 mL×3). The combined organic phases were washed with 1N aqueous hydrochloric acid (300 mL×3) and brine (300 mL×1), dried over anhydrous sodium sulfate, and concentrated to afford (S)-2-(tert-butoxycarbonylamino)-3-(4-chlorobutanamido)propanoic acid (15.5 g, 64% yield), which was used directly without further purification.

후처리

  1. temperatureto warm to ambient temperature
  2. stirringstirred overnight
  3. extractionextracted with EtOAc (300 mL×3)
  4. washThe combined organic phases were washed with 1N aqueous hydrochloric acid (300 mL×3) and brine (300 mL×1)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8d72f0c3ca4c40a4a38d5aa1be72d397
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434761B2

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