2,2-Dimethoxypropane → HCID 59396014, compound

HRID 1094761Notes

Reaction equation

HRID 1094761 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:7][C:8](=[O:18])[CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:4][CH:5]=[CH2:6].CO[C:21](OC)([CH3:23])[CH3:22].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(Cl)Cl.CO>C1(C)C=CC=CC=1>[CH3:22][C:21]1([CH3:23])[N:7]([C:8](=[O:18])[CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[C@@H:3]([CH2:4][CH:5]=[CH2:6])[CH2:2][O:1]1

Participants

6

Reactant 4

HCID 64952,2-DimethoxypropaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 21226129Dichloromethane methanolHCID 59396016HCID 59396016, compound

Product 1

HCID 59396014HCID 59396014, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of 1,1-dimethylethyl (2-{[(1S)-1-(hydroxymethyl)-3-buten-1-yl]amino}-2-oxoethyl)carbamate D21 (37 g) in toluene (370 ml) stirred at 25° C. were added 2,2-bis(methyloxy)propane (370 ml, 3020 mmol) and p-toluenesulfonic acid monohydrate (3.7 g, 19.45 mmol). The reaction mixture was stirred at reflux (85° C. internal, oil bath 105° C.) for 1.5 hour (clear solution). The check by TLC (DCM/MeOH 95/5) showed the reaction to be completed. The solvent was evaporated to obtain a brown oil that was chromatographed (Biotage 75 L, silica, eluting with Cy/EtOAc 8/2, 7/3) to give the title compound D22 (30 g) as yellow oil. UPLC (Acid GEN_QC): rt=0.69 minutes, peak observed: 299 (M+1). C15H26N2O4 requires 298. 1H NMR (400 MHz, CDCl3) δ ppm 1.46 (s, 9 H) 1.54 (s, 3 H) 1.67 (s, 3 H) 2.30-2.49 (m, 2 H) 3.71-4.05 (m, 5 H) 5.04-5.22 (m, 2 H) 5.37-5.52 (m, 1 H) 5.65-5.81 (m, 1 H)

Workup

  1. stirringThe reaction mixture was stirred
  2. temperatureat reflux (85° C. internal, oil bath 105° C.) for 1.5 hour (clear solution)
  3. customthe reaction
  4. customThe solvent was evaporated
  5. customto obtain a brown oil that
  6. customwas chromatographed
  7. wash(Biotage 75 L, silica, eluting with Cy/EtOAc 8/2, 7/3)

Sources & evidence

ORD record
ord-b0aae414a56742b9a3bbfcab5bd9014b
Source dataset
uspto-grants-2012_03
Patent number
US08133908B2

Reaction notes

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