Trifluoroacetic acid → HCID 67086777, compound

HRID 2365488Notes

Reaction equation

HRID 2365488 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:30][NH2:31])[CH2:9][C:10]([CH3:29])([CH3:28])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C@@H:21]2[CH2:25][O:24]C(C)(C)[O:22]2)=[CH:15][CH:14]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][C@H:8]([CH2:30][NH2:31])[CH2:9][C:10]([CH3:28])([CH3:29])[CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C@@H:21]([OH:22])[CH2:25][OH:24])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67120682HCID 67120682, compound

Product 1

HCID 67086777HCID 67086777, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {(S)-1-Aminomethyl-5-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-3,3-dimethyl-pentyl}-carbamic acid tert-butyl ester (0.13 g, 0.28 mmol) and TFA (1 ml) in DCM (5 ml) is stirred at room temperature for 1 hour, then loaded onto an SCX-2 cartridge which has been pre-eluted with MeOH. The cartridge is eluted with MeOH (2×5 ml), followed by 7M NH3 in MeOH (2×5 ml) to yield (S)-3-[4-((S)-5,6-Diamino-3,3-dimethyl-hexyl)-phenoxy]-propane-1,2-diol in 80% purity as a colourless oil; [M+H]+ 311

Workup

  1. washhas been pre-eluted with MeOH
  2. washThe cartridge is eluted with MeOH (2×5 ml)

Sources & evidence

ORD record
ord-b8aa49925efa4db2998e53ebaa9628db
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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