Water → HCID 131735613, compound

HRID 529286Notes

Reaction equation

HRID 529286 reaction equation
[NH2:1][C@@H:2]([CH2:15][CH2:16][CH3:17])[C:3]([O:12][CH2:13][CH3:14])([O:9][CH2:10][CH3:11])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:18](Cl)([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].O>C1COCC1>[CH2:21]([O:20][C:18]([NH:1][C@@H:2]([CH2:15][CH2:16][CH3:17])[C:3]([O:9][CH2:10][CH3:11])([O:12][CH2:13][CH3:14])[C:4]([O:6][CH2:7][CH3:8])=[O:5])=[O:19])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10387Benzyl chloroformateHCID 131735614HCID 131735614, compound

Product 1

HCID 131735613HCID 131735613, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (S)-ethyl 3-amino-2,2-diethoxyhexanoate (prepared analogously to examples 1, 10, 11 and 15) (1000 mg, 4 mmol) in THF (20 mL) at ambient temperature was added K2OC3 (829 mg, 6 mmol), followed by CbzCl (628 μL, 4.4 mmol). After 20 h water was added and the aqueous layer was extracted with Et2O. The combined organic layers were dried and the solvent was removed under reduced pressure. Column chromatography (silicagel, cyclohexane:EtOAc 10:1→5:1) gave 1000 mg of the carbamate.

Workup

  1. additionwas added K2OC3 (829 mg, 6 mmol)
  2. extractionthe aqueous layer was extracted with Et2O
  3. customThe combined organic layers were dried
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-bb93aaccd0354e42b8c2f4e1c1f1e3b9
Source dataset
uspto-grants-2016_05
Patent number
US09346853B2

Reaction notes

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