Hydrochloric Acid → Ethyl 2-amino-3-oxo-3-(tetrahydrofuran-3-yl)propanoate, hydrochloride salt

HRID 1427352

반응식

HRID 1427352 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1(C(/[N:24]=[CH:25]/[C:26]([O:28][CH2:29][CH3:30])=[O:27])C2C=CC=CC=2)C=CC=CC=1.[O:31]1[CH2:35][CH2:34][CH:33]([C:36]([Cl:38])=[O:37])[CH2:32]1.Cl>O1CCCC1>[ClH:38].[NH2:24][CH:25]([C:36](=[O:37])[CH:33]1[CH2:34][CH2:35][O:31][CH2:32]1)[C:26]([O:28][CH2:29][CH3:30])=[O:27]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 2733832Lithium HexamethyldisilazideHCID 14020412Tetrahydrofuran-3-carbonyl chlorideHCID 178472686HCID 178472686, 화합물

생성물 1

HCID 131732346Ethyl 2-amino-3-oxo-3-(tetrahydrofuran-3-yl)propanoate, hydrochloride salt

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Lithium bis(trimethysilyl)amide (1 M solution in tetrahydrofuran, 288 mL, 0.288 mol) was added drop-wise to a solution of ethyl (2E)-[(diphenylmethyl)imino]ethanoate (70 g, 0.26 mol) in tetrahydrofuran (1 L) at −70° C. The reaction mixture was stirred for 30 minutes, and the resulting suspension was transferred via cannula into a solution of tetrahydrofuran-3-carbonyl chloride (35.7 g, 0.26 mol) in tetrahydrofuran (200 mL) at −70° C. The reaction mixture was stirred at room temperature for 2 hours, at which time aqueous hydrochloric acid (2 M, 260 mL) was added. After the reaction mixture had stirred for 15 minutes, the tetrahydrofuran was removed in vacuo, and the aqueous residue was washed with ethyl acetate (4×200 mL). The aqueous layer was freeze-dried, affording the product as a light yellow solid. Yield: 40 g, 0.20 mol, 77%.

후처리

  1. additionwas added
  2. stirringAfter the reaction mixture had stirred for 15 minutes
  3. customthe tetrahydrofuran was removed in vacuo
  4. washthe aqueous residue was washed with ethyl acetate (4×200 mL)
  5. customThe aqueous layer was freeze-dried

출처 및 근거

ORD 기록
ord-5184103b253c454696c48cdd15f20b7b
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933224B2

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