Isopropyl chloroformate → HCID 67441573, compound

HRID 1664216Notes

Reaction equation

HRID 1664216 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:12]=[C:11]([NH:13][C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH:10]=[C:6](C(O)=O)[CH:5]=1.CCN(CC)CC.[CH:32]([O:35]C(Cl)=O)(C)C.[BH4-].[Na+]>C1COCC1.CN1CCCC1=O.C(OCC)C.O>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:5]=[CH:6][CH2:10][C:11]([NH:13][C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])([CH2:32][OH:35])[CH:12]=1

Participants

9

Reactant 4

HCID 7917Isopropyl chloroformateHCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 67440676HCID 67440676, compound

Product 1

HCID 67441573HCID 67441573, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolvent3×HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
0 °C

Procedure

5-Benzyloxycarbonylamino-isophthalic acid monomethyl ester (10 g, 30.1 mmol, 1 eq) and Et3N (5 ml, 36.1 mmol, 1.2 eq) are suspended in a mixture of THF (200 ml) and N-methylpyrrolidone (200 ml). Isopropylchloroformate (42 ml, 1 N in toluene, 42 mmol, 1.4 eq) is added, and the reaction mixture is stirred for 30 min at 0° C. and then diluted with diethyl ether and water. The organic layer is washed with 0.1 N HCl and brine. NaBH4 (3.82 g, 101 mmol, 3.36 eq) is dissolved in H2O (100 ml), and the solution is added to the reaction mixture, which is then stirred for 1 h. Diethyl ether and H2O are added, and the organic layer is separated, washed with brine, dried over sodium sulfate, filtered and concentrated. The residue is purified by column chromatography using EtOAc/hexane in a ratio of 1 to 2 to give the product.

Workup

  1. washThe organic layer is washed with 0.1 N HCl and brine
  2. additionthe solution is added to the reaction mixture, which
  3. stirringis then stirred for 1 h
  4. customthe organic layer is separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue is purified by column chromatography
  10. customto give the product

Sources & evidence

ORD record
ord-eff0631a95594f8aa4816f5c2a162510
Source dataset
uspto-grants-2011_10
Patent number
US08039455B2

Reaction notes

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