Hydrochloric Acid → HCID 22949352, compound

HRID 849826Notes

Reaction equation

HRID 849826 reaction equation
CC(C)([O-:4])C.[K+].[C:7]([O:11][C:12]([NH:14][C:15]([CH3:19])([CH3:18])[CH:16]=O)=[O:13])([CH3:10])([CH3:9])[CH3:8].Cl.[O:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>>[CH2:22]([O:21][C:25](=[O:4])/[CH:24]=[CH:16]/[C:15]([NH:14][C:12]([O:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:13])([CH3:19])[CH3:18])[CH3:23]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14578674tert-butyl N-(2-methyl-1-oxopropan-2-yl)carbamateHCID 23665647Potassium tert-butoxide

Product 1

HCID 22949352HCID 22949352, compound

Procedure

Triethyl phosphonoacetate (9.6 ml, 48 mmol ) was added slowly to a suspension of potassium tert-butoxide (5.39 g, 48 mmol) in tetrahydrofuran (140 ml). After 30 min at 20° C. 2-tert-butoxycarbonylamino-2-methylpropanal (5.0 g, 26 mmol) was added. After 2.5 h at 20° C. 1N hydrochloric acid (80 ml) was added slowly. The mixture was extracted with ethyl acetate (120 ml, 2×50 ml) and the combined organic layers were washed with a saturated solution of sodium hydrogencarbonate (100 ml) and dried (magnesium sulfate). The solvent was removed in vacuo and the crude product was chromatographed on silica gel (100 g) with ethyl acetate/heptane 1:4 as eluent to give 5.7 g of (2E)-4-tert-butoxycarbonylamino-4-methylpent-2-enoic acid ethyl ester.

Workup

  1. waitAfter 2.5 h at 20° C
  2. extractionThe mixture was extracted with ethyl acetate (120 ml, 2×50 ml)
  3. washthe combined organic layers were washed with a saturated solution of sodium hydrogencarbonate (100 ml)
  4. dry with materialdried (magnesium sulfate)
  5. customThe solvent was removed in vacuo
  6. customthe crude product was chromatographed on silica gel (100 g) with ethyl acetate/heptane 1:4 as eluent

Sources & evidence

ORD record
ord-84220930d7d94f5f86547934a78e9934
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

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