Water → HCID 178452464, compound

HRID 710266Notes

Reaction equation

HRID 710266 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.[F:21][C:22]1[CH:35]=[CH:34][C:25]([C:26](Cl)=[N:27]OS(C)(=O)=O)=[CH:24][CH:23]=1.CN(C)CCN(C)C.O>O1CCCC1>[F:21][C:22]1[CH:35]=[CH:34][C:25]([C:26]2[NH:1][C:2]3[CH:3]=[CH:4][C:5]([C@@H:8]4[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]4)=[CH:6][C:7]=3[N:27]=2)=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 541196854-fluoro-N-(methylsulfonyloxy)benzimidoyl chlorideHCID 66705988(S)-Tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate

Product 1

HCID 178452464HCID 178452464, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate (140 mg, 0.5 mol), 4-fluoro-N-(methylsulfonyloxy)benzimidoyl chloride (152 mg, 0.6 mmol) and N,N,N′,N′-tetramethylethylenediamine (123 mg, 1.06 mmol) in tetrahydrofurane (0.8 ml) was shaken in a closed vial at 60° C. overnight. Water was added, and the mixture was extracted twice with ethyl acetate. The cobined organic layers were dried (MgSO4) and evaporated. Flash chromatography (10 g silica gel, 10 to 30% ethyl acetate in heptane) yielded a white solid (92 mg, 46%), MS (ISP): 398.2 ([M+H]+).

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. dry with materialThe cobined organic layers were dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-540e2abc9d024860a42710f25a74755f
Source dataset
uspto-grants-2015_11
Patent number
US09181230B2

Reaction notes

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