tert-Butyl acetate → HCID 14986687, compound

HRID 1494129Notes

Reaction equation

HRID 1494129 reaction equation
C1(NC(C)C)CCCCC1.C([Li])CCC.[C:16]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])[CH3:17].[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([NH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH:39]([CH2:42][CH2:43][CH2:44][O:45][CH:46]2[CH2:51][CH2:50][CH2:49][CH2:48][O:47]2)[CH2:40]I)(=[O:33])=[O:32])=[CH:27][CH:26]=1>O1CCCC1.CCCCCC.CN(C)P(N(C)C)(N(C)C)=O>[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([S:31]([NH:34][CH2:35][CH2:36][CH2:37][CH2:38][CH:39]([CH2:42][CH2:43][CH2:44][O:45][CH:46]2[CH2:51][CH2:50][CH2:49][CH2:48][O:47]2)[CH2:40][CH2:17][C:16]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])(=[O:32])=[O:33])=[CH:29][CH:30]=1

Participants

8

Reactant 4

HCID 10908tert-Butyl acetateHCID 62386CyclohexylisopropylamineHCID 14986686HCID 14986686, compoundHCID 178418339Butyllithium

Product 1

HCID 14986687HCID 14986687, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 0.11 mL cyclohexyl-isopropylamine (0.68 mmol) in 1 mL dry tetrahydrofuran at 0° C. is added dropwise 0.23 mL (0.57 mmol) of a 2.5 M solution of n-butyllithium in hexane. The mixture is allowed to stir for 15 minutes at 0° C. The reaction mixture is then cooled to -78° C. and 0.077 mL (0.57 mmol) t-butyl acetate is added and the mixture is stirred at -78° C. for 0.5 hour. Then a solution of 0.12 g (0.22 mmol) of 6-(p-chlorophenylsulfonamido)-2-[3-(tetrahydropyranyloxy)propyl]-1-iodohexane in 0.5 mL hexamethylphosphoramide is added followed by 1 ml dry tetrahydrofuran. The reaction temperature is raised to -23° C. and allowed to warm to 0° C. over a period of 1 hour. The reaction is then quenched by the addition of 5 mL saturated aqueous ammonium chloride solution and extracted with ether. The organic layer is washed with water (3×25 mL) and brine, dried, filtered, and concentrated to give a yellow oil which is chromatographed using 3:7 ethyl acetate, hexane to yield t-butyl 8-(p-chlorophenylsulfonamido)-4-[3-(tetrahydropyranyloxy)propyl]-octanoate; NMR (CDCl3): delta 2.2 (t,2H), 1.6 (s,9H); IR (neat): 1721 cm-1.

Workup

  1. temperatureThe reaction mixture is then cooled to -78° C.
  2. stirringthe mixture is stirred at -78° C. for 0.5 hour
  3. temperatureThe reaction temperature is raised to -23° C.
  4. temperatureto warm to 0° C. over a period of 1 hour
  5. customThe reaction is then quenched by the addition of 5 mL saturated aqueous ammonium chloride solution
  6. extractionextracted with ether
  7. washThe organic layer is washed with water (3×25 mL) and brine
  8. customdried
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give a yellow oil which
  12. customis chromatographed

Sources & evidence

ORD record
ord-0a5e915cc8a74750b0935d091780a987
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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