Hydrochloric Acid → 10-tert-Butoxycarbonylamino-3-(2-methyl-pyrimidin-5-yl)-dec-4-enoic acid ethyl ester

HRID 860095Notes

Reaction equation

HRID 860095 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13](O)[CH:14]=[CH:15][C:16]1[CH:17]=[N:18][C:19]([CH3:22])=[N:20][CH:21]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)CC.Cl.[C:31](OCC)([O:36]CC)([O:33][CH2:34][CH3:35])[CH3:32]>[Cl-].[Na+].O>[CH2:34]([O:33][C:31](=[O:36])[CH2:32][CH:15]([C:16]1[CH:17]=[N:18][C:19]([CH3:22])=[N:20][CH:21]=1)[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:24])[CH3:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1032Propionic AcidHCID 66221Triethyl orthoacetateHCID 73687171[6-Hydroxy-8-(2-methyl-pyrimidin-5-yl)-oct-7-enyl]-carbamic acid tert-butyl ester

Product 1

HCID 6966645410-tert-Butoxycarbonylamino-3-(2-methyl-pyrimidin-5-yl)-dec-4-enoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
150 °C

Procedure

A solution of 24-4 (1.00 g, 2.98 mmol) in triethyl orthoacetate (50 mL) was treated with propionic acid (2.5 mg, 0.034 mmol) and heated to 150° C. for 3 h. The reaction mixture was cooled to room temperature and treated with 1 N HCl and brine (75 mL each). The mixture was extracted with two portions of ethyl acetate. The combined organics were washed with brine and dried (Na2SO4). Purification via PCTLC (SiO2, 4 mm, 10% EtOH; 90% CH2Cl2) afforded 24-5 (650 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe mixture was extracted with two portions of ethyl acetate
  3. washThe combined organics were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customPurification via PCTLC (SiO2, 4 mm, 10% EtOH; 90% CH2Cl2)

Sources & evidence

ORD record
ord-dd95499552944caba5e9f930125ba7e1
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

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