Hydrochloric Acid → HCID 90162827, compound

HRID 709334Notes

Reaction equation

HRID 709334 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([N:17]1[CH:21]=[C:20]([C@@:22]([NH:27][C:28]([C:30]2[CH:34]=[CH:33][S:32][CH:31]=2)=[O:29])([CH:24]([CH3:26])[CH3:25])[CH3:23])[N:19]=[N:18]1)[C:14](O)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.[Cl:42][C:43](OCC(C)C)=O.[N+](=C)=[N-].Cl>C1COCC1.O.C(OCC)(=O)C.C(O)(=O)C>[Cl:42][CH2:43][C:14](=[O:15])[C@@H:13]([N:17]1[CH:21]=[C:20]([C@@:22]([NH:27][C:28]([C:30]2[CH:34]=[CH:33][S:32][CH:31]=2)=[O:29])([CH:24]([CH3:26])[CH3:25])[CH3:23])[N:19]=[N:18]1)[CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 9550DiazomethaneHCID 62365Isobutyl chloroformateHCID 90150483HCID 90150483, compound

Product 1

HCID 90162827HCID 90162827, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of carboxylic acid 9 (50 mg, 100.9 μmol) in 5 ml dry THF under argon atmosphere at −60° C. was added N-methylmorpholine (14 μl, 126.3 μmol, 1.25 equiv.) and isobutyl chloroformate (14.9 μl, 116.7 μmol, 1.15 equiv.). After 30 min an etheral solution of diazomethane (0.95 ml 0.6 M, 0.57 mmol, 5.6 equiv.) was added to above solution at −60° C. and the reaction mixture was stirred for 1 hr. A 1:1 solution of conc. HCl and glacial acetic acid was added dropwise to the reaction mixture, before ethyl acetate and water were added. The organic layer was washed with brine, sat. aq. NaHCO3 and dried over MgSO4. Concentration in vacuo afforded the crude title compound, which was used without purification. 1H NMR (400 MHz, CDCl3+MeOD) δ ppm 7.89 (dd, J=1.5 Hz, J=3.0 Hz, 1H), 7.71 (s, 1H), 7.39 (dd, J=1.2 Hz, J=5.2 Hz, 1H), 7.36 (dd, J=2.9 Hz, J=5.2 Hz, 1H), 7.06 (s, 1H), 5.59 (dd, J=4.6 Hz, J=10.0 Hz, 1H), 4.80 (s, 1H), 4.17 (s, 2H), 3.06 (m, 2H), 2.83 (m, 2H), 2.30 (m, 1H), 2.11 (m, 1H), 1.88 (s, 3H), 1.48 (m, 2H), 1.42 (s, 9H), 1.34 (m, 1H), 1.22 (m, 1H), 0.99 (d, J=6.8 Hz, 3H), 0.80 (d, J=6.8 Hz, 3H). MS (ESI): m/z calcd for C24H36C1N5O4S+H+ 526.2 [M+H]+. found 526.3.

Workup

  1. additionwere added
  2. washThe organic layer was washed with brine, sat. aq. NaHCO3
  3. dry with materialdried over MgSO4
  4. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-0fb7ea65cbf24559982dbbafb3fe2965
Source dataset
uspto-grants-2015_11
Patent number
US09180209B2

Reaction notes

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