Trifluoroacetic acid → HCID 53852269, compound

HRID 1953914Notes

Reaction equation

HRID 1953914 reaction equation
C(O[C:6](=O)[N:7]([CH:9]([C:14](=[O:39])[NH:15][CH:16]([C:32](=[O:38])[NH:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:20][CH:19]=1)[CH2:10][CH:11]([CH3:13])[CH3:12])C)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:25]([O:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][CH:16]([NH:15][C:14](=[O:39])[CH:9]([NH:7][CH3:6])[CH2:10][CH:11]([CH3:12])[CH3:13])[C:32](=[O:38])[NH:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[CH:19][CH:20]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53877102HCID 53877102, compound

Product 1

HCID 53852269HCID 53852269, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[S-(R*,R*)]-{1-[2-(4-Benzyloxy-phenyl)-1-tert-butylcarbamoyl-ethylcarbamoyl]-3-methyl-butyl}-methyl-carbamic acid tert-butyl ester (4.0 g, 7.24 mmol) was dissolved in CH2Cl2 (24 mL) and treated with trifluoroacetic acid (16 mL). The reaction was stirred for 15 minutes, then concentrated, diluted with EtOAc (300 mL), washed with bicarbonate solution (3×300 mL) and brine (300 mL), dried over Na2SO4, and concentrated. The crude material was chromatographed on silica gel eluting with 8% MeOH/CH2Cl2 to give 2.8 g (85%) of [S-(R*,R*)]-4-methyl-2-methylamino-pentanoic acid [2-(4-benzyloxy-phenyl)-1-tert-butylcarbamoyl-ethyl]-amide.

Workup

  1. concentrationconcentrated
  2. additiondiluted with EtOAc (300 mL)
  3. washwashed with bicarbonate solution (3×300 mL) and brine (300 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude material was chromatographed on silica gel eluting with 8% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-5ef4e36e769941379863493013d59823
Source dataset
uspto-grants-2000_09
Patent number
US06117841

Reaction notes

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