Trifluoroacetic acid → 4-[2-Cyclohexyl-2-(2-methylamino-propionylamino)-acetyl]-1-methanesulfonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid (1,2,3,4-tetrahydro-naphthalen-1-yl)-amide

HRID 446965Notes

Reaction equation

HRID 446965 reaction equation
C(O[C:6](=O)[N:7]([CH:9]([C:11](=[O:47])[NH:12][CH:13]([CH:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1)[C:14]([N:16]1[CH2:20][CH2:19][CH:18]2[N:21]([S:37]([CH3:40])(=[O:39])=[O:38])[CH2:22][CH:23]([C:24](=[O:36])[NH:25][CH:26]3[C:35]4[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH2:29][CH2:28][CH2:27]3)[CH:17]12)=[O:15])[CH3:10])C)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:26]1([NH:25][C:24]([CH:23]2[CH2:22][N:21]([S:37]([CH3:40])(=[O:38])=[O:39])[CH:18]3[CH2:19][CH2:20][N:16]([C:14](=[O:15])[CH:13]([CH:41]4[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]4)[NH:12][C:11](=[O:47])[CH:9]([NH:7][CH3:6])[CH3:10])[CH:17]23)=[O:36])[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67281619(1-{1-Cyclohexyl-2-[4-methanesulfonyl-6-(1,2,3,4-tetrahydro-naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethylcarbamoyl}-ethyl)-methyl-carbamic acid tert-butyl ester

Product 1

HCID 672806554-[2-Cyclohexyl-2-(2-methylamino-propionylamino)-acetyl]-1-methanesulfonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid (1,2,3,4-tetrahydro-naphthalen-1-yl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 22 (222 mg, 0.3 mmol) in DCM (10 mL) was treated with TFA (3 mL) at ambient temperature. After 1.5 h, the solution was concentrated, diluted with EtOAc, washed with saturated NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated. The resulting residue was diluted with ACN/H2O containing 0.1% HOAc and purified by reverse-phase HPLC (2″ Dynamax® C18, 10-100% ACN/H2O containing 0.1% HOAc). The product-containing fractions were frozen and lyophilized to afford 23 as a white solid.

Workup

  1. concentrationthe solution was concentrated
  2. additiondiluted with EtOAc
  3. washwashed with saturated NaHCO3
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionThe resulting residue was diluted with ACN/H2O containing 0.1% HOAc
  8. custompurified by reverse-phase HPLC (2″ Dynamax® C18, 10-100% ACN/H2O containing 0.1% HOAc)
  9. temperatureThe product-containing fractions were frozen

Sources & evidence

ORD record
ord-32a88e702bad4b658f25e44d7572820d
Source dataset
uspto-grants-2013_07
Patent number
US08481495B2

Reaction notes

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