Hydrochloric Acid → HCID 70048334, compound

HRID 1110464Notes

Reaction equation

HRID 1110464 reaction equation
Cl.C([O:6][C:7](=[O:69])[C@H:8]([CH2:57][C:58]1[CH:63]=[CH:62][C:61]([O:64]C(C)(C)C)=[CH:60][CH:59]=1)[NH:9][C:10]([C:12]1([CH2:17][C@H:18]([C:50]([O:52]C(C)(C)C)=[O:51])[CH2:19][NH:20][C:21](=[O:49])[C@H:22]([CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:40])[NH:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])(C)(C)C.C1(OC)C=CC=CC=1>ClCCl>[CH2:27]([O:26][C:24]([NH:23][C@H:22]([C:21]([NH:20][CH2:19][C@@H:18]([C:50]([OH:52])=[O:51])[CH2:17][C:12]1([C:10]([NH:9][C@H:8]([C:7]([OH:69])=[O:6])[CH2:57][C:58]2[CH:63]=[CH:62][C:61]([OH:64])=[CH:60][CH:59]=2)=[O:11])[CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:49])[CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:39]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:40])=[O:25])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 54023343HCID 54023343, compound

Product 1

HCID 70048334HCID 70048334, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Hydrogen chloride gas was passed through a stirred, ice cold solution of N-{1-[3-(N2,N6 -dibenzyloxycarbonyl-(S)-lysylamino)-2-t- butryloxycarbonylpropyl]-1-cyclopentanecarbonyl}-O-t-butyl-(S)- tyrosine-t-butyl ester (from Example 81, 0.445 g, 0.47 mmole), and anisole (0.765 g, 7.1 mmole) in dry dichloromethane (10 ml) until saturation was achieved. A precipitate formed. After stirring for 1.5 hours, the solvent was evaporated under reduced pressure, and the residue azeotroped with dry dichloromethane. The residue was partitioned between ethyl acetate and aqueous sodium bicarbonate. The phases were separated, and the organic phase washed with two further portions of aqueous sodium bicarbonate. The combined aqueous phases were re-extracted with diethyl ether, and then acidified with 1M hydrochloric acid to pH 2. The aqueous phase was extracted with ethyl acetate (2x) and the combined organic phases dried (MgSO4), filtered and the solvent evaporated to yield a foam, which was azeotroped with methylene chloride to yield the title compound as a solid foam (0.325 g, 89%). Found: C,62.81; H,6.68; N,6.92. C41H50N4O11 0.4 CH2Cl2 requires C.61.17; H,6.33; N,6.93%.

Workup

  1. customA precipitate formed
  2. customthe solvent was evaporated under reduced pressure
  3. customthe residue azeotroped with dry dichloromethane
  4. customThe residue was partitioned between ethyl acetate and aqueous sodium bicarbonate
  5. customThe phases were separated
  6. washthe organic phase washed with two further portions of aqueous sodium bicarbonate
  7. extractionThe combined aqueous phases were re-extracted with diethyl ether
  8. extractionThe aqueous phase was extracted with ethyl acetate (2x)
  9. dry with materialthe combined organic phases dried (MgSO4)
  10. filtrationfiltered
  11. customthe solvent evaporated
  12. customto yield a foam, which
  13. customwas azeotroped with methylene chloride

Sources & evidence

ORD record
ord-e5727fa9e8604c588f588a34cf491fb8
Source dataset
uspto-grants-1990_12
Patent number
US04975444

Reaction notes

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