Methanol → Methyl 2-[(tert-butoxycarbonyl)amino]pent-4-ynoate

HRID 433822Notes

Reaction equation

HRID 433822 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CO.[CH2:9]([O:16][C:17](=[O:30])[CH:18]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:20]=O)C1C=CC=CC=1.COP(C(=[N+]=[N-])C(=O)C)(=O)OC>C(OCC)C>[CH3:9][O:16][C:17](=[O:30])[CH:18]([NH:22][C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH2:19][C:20]#[CH:1]

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 143577952-Tert-butoxycarbonylamino-4-oxo-butyric acid benzyl esterHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 10537281Methyl 2-[(tert-butoxycarbonyl)amino]pent-4-ynoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Potassium carbonate (1.687 g, 12.2 mmol) was added to an anhydrous methanol (91.5 mL) solution of 2-tert-butoxycarbonylamino-4-oxo-butyric acid benzyl ester (1.875 g, 6.10 mmol) and the reaction stirred 10 minutes. (1-Diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (1.407 g, 7.32 mmol) was added and the reaction was stirred at room temp temperature 1 hour. The reaction was poured into diethyl ether and washed 4 times with 5% sodium bicarbonate, dried over magnesium sulfate and concentrated (1.05 g, crude product mixture). The crude product was used directly in the next step. 1H NMR (400 MHz, CDCl3) δ5.39 -5.31 (m, 1H), 4.49-4.41 (m, 1H), 3.77 (s, 3H), 2.79-2.65 (m, 2H), 2.03 (s, 1H), 1.59 and 1.44 (2 singlets, rotamers, 3H).

Workup

  1. stirringthe reaction was stirred at room temp temperature 1 hour
  2. washwashed 4 times with 5% sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated (1.05 g, crude product mixture)

Sources & evidence

ORD record
ord-bee6c401593f4459a90d3eeb29bfdb45
Source dataset
uspto-grants-2003_12
Patent number
US06668527B2

Reaction notes

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