Hydrochloric Acid → HCID 86588667, compound

HRID 1726446Notes

Reaction equation

HRID 1726446 reaction equation
Cl.C(OC(=O)[NH:8][CH2:9][CH2:10][CH2:11][C:12](=[O:16])[NH:13][CH2:14][CH3:15])(C)(C)C.[C:18]([NH:25][CH2:26][CH2:27][CH2:28][C:29]([OH:31])=O)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>CO.CN(C=O)C>[C:21]([O:20][C:18](=[O:19])[NH:25][CH2:26][CH2:27][CH2:28][C:29](=[O:31])[NH:8][CH2:9][CH2:10][CH2:11][C:12](=[O:16])[NH:13][CH2:14][CH3:15])([CH3:22])([CH3:23])[CH3:24]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2948944-(((Tert-butoxy)carbonyl)amino)butanoic acidHCID 11138962(3-Ethylcarbamoyl-propyl)-carbamic acid tert-butyl ester

Product 1

HCID 86588667HCID 86588667, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Hydrochloric acid (12%, 64 ml) was added to a cold solution of Boc-derivative 3 (21.1 g, 91.7 mmol) in MeOH (190 ml) and stirred overnight at room temperature. The next day additional acid (30 ml) was added and stirring was continued for another 10 h. The reaction mixture was filtered, washed with CHCl3, concentrated and dried in vacuo overnight. The product was suspended in DMF (300 ml) with DIEA (42 ml), cooled to 0° C. and a solution of Bt-derivative 2 (29 g, 90.5 mmol) in DMF (100 ml) was added into the reaction mixture. The cooling bath was removed and the stirring was continued overnight. The solvent and DIEA were removed in vacuo at 45° C., the residue was suspended in CHCl3/H2O mixture, washed with H2O, aq. KHSO4 (20%), H2O, aq. NaHCO3 (2 times with each), dried (Na2SO4), concentrated in vacuo, and triturated with petr. ether. Yield 22.32 g (78%). mp: 134-1350. 1H (CDCl3): 1.15 (t, J=7.27, 3H), 1.44 (s, 9H), 1.65-1.95 (m, 4H), 2.20-2.26 (m, 4H), 3.19 (q, J=6.15, 2H), 3.23-3.35 (m, 4H), 4.82 (bs, 1H), 6.40 (bs, 1H), 6.68 (bs, 1H). 13C (CDCl3): 14.77, 24.92, 25.66, 26.43, 28.38, 33.59, 33.84, 33.92, 34.35, 38.83, 39.66, 79.35, 156.56, 172.65, 173.12. ESI-MS: 338.2 (MNa+), 316.0 (MH+), 216.0 (MH+-Boc).

Workup

  1. stirringstirring
  2. waitwas continued for another 10 h
  3. filtrationThe reaction mixture was filtered
  4. washwashed with CHCl3
  5. concentrationconcentrated
  6. customdried in vacuo overnight
  7. temperaturecooled to 0° C.
  8. customThe cooling bath was removed
  9. waitthe stirring was continued overnight
  10. customThe solvent and DIEA were removed in vacuo at 45° C.
  11. washwashed with H2O, aq. KHSO4 (20%), H2O, aq. NaHCO3 (2 times with each),
  12. dry with materialdried (Na2SO4)
  13. concentrationconcentrated in vacuo
  14. customtriturated with petr

Sources & evidence

ORD record
ord-d73d1136bb5e489f95ba590cd3b1f5ea
Source dataset
uspto-grants-2009_02
Patent number
US07491849B2

Reaction notes

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