Methyl chloroformate → HCID 59191808, compound

HRID 1515552Notes

Reaction equation

HRID 1515552 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:20][CH:21]2[CH2:23][CH2:22]2)=[C:6]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:7]=1.Cl[C:25]([O:27][CH3:28])=[O:26]>N1C=CC=CC=1>[CH:21]1([S:20][C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:25]([O:27][CH3:28])=[O:26])=[CH:7][C:6]=2[C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:22][CH2:23]1

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 59479442HCID 59479442, compound

Product 1

HCID 59191808HCID 59191808, compoundYield 109%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 85G (1.25 g, 3.74 mmol) in pyridine (8.0 mL) at 0° C. was added methyl chloroformate (0.4 mL, 5.23 mmol). After 30 min, the reaction was quenched by MeOH (2.0 mL). Pyridine was removed under high vacuum. The crude was suspended in EtOAc and washed by 1.0 N HCl (2×20 mL), sat. NaHCO3 and brine. The organic layer was dried over Na2SO4. After evaporation of solvent, 85H (1.6 g, 95% yield) was obtained as a solid used for next step without purification. 1H NMR (400 MHz, DMSO-d6, 100° C.) δ ppm 0.52-0.64 (m, 2H) 0.94-1.05 (m, 2H) 1.17-1.28 (s, 9H) 1.54-1.63 (m, 1H) 1.77-1.86 (m, 2H) 2.18-2.29 (m, 2H) 3.46-3.57 (m, 2H) 3.62-3.68 (s, 3H) 5.05 (dd, J=7.70, 3.85 Hz, 1H) 7.23 (s, 1H) 7.32-7.40 (m, 1H) 7.40-7.47 (m, 1H) 9.26 (s, 1H), LC-MS 293 (M-Boc).

Workup

  1. customthe reaction was quenched by MeOH (2.0 mL)
  2. customPyridine was removed under high vacuum
  3. washwashed by 1.0 N HCl (2×20 mL), sat. NaHCO3 and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customAfter evaporation of solvent

Sources & evidence

ORD record
ord-d4308a0446da4712b59b8ccdd93bbce5
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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