HCID 69221606, compound → N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(sec-butoxy)-4-methoxybenzene-sulfonamide

HRID 29181Notes

Reaction equation

HRID 29181 reaction equation
[CH2:1]([C@H:8]([NH:29]C(=O)OC(C)(C)C)[C@@H:9]([OH:28])[CH:10]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=[O:19])=[O:18])OC(CC)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[NH2:29][C@@H:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@H:9]([OH:28])[CH2:10][N:16]([O:26][CH:23]([CH2:22][CH3:21])[CH3:24])[S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=[O:18])=[O:19]

Participants

3

Reactant 1

HCID 69221606HCID 69221606, compound

Product 1

HCID 57264501N-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(sec-butoxy)-4-methoxybenzene-sulfonamide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-butyl N-((1S,2R)-1-benzyl-3-sec-butoxy[(4-methoxyphenyl)sulfonyl]amino-2-hydroxy-propyl)carbamate (1.9 mmol, 1 g) was stirred in neat trifluoroacetic acid (TFA) at room temperature for 1 hour. The TFA was removed under vacuum, and the resulting residue was dissolved in ethyl acetate, washed with 5% aq. potassium carbonate solution, brine and dried over magnesium sulfate. The dried solution was concentrated under vacuum and stored as a sticky white solid. H1-NMR (CDCl3): δ 7.81 (2H,d), 7.28-7.16 (5H,m), 7.01 (2H,d), 4.31 (2H,bs), 4.01-3.90 (1H,bs), 3.88 (3H,s), 3.5-2.5 (1H,bs), 3.33(2H,bs), 2.89 (2H,bs), 2.63(2H,bs), 1.71 (1H,bs), 1.43-1.40 (1H,m), 1.27-1.19 (3H,m), 0.98-0.85 (3H,m); MS (ESI): M+H=423.

Workup

  1. customThe TFA was removed under vacuum
  2. dissolutionthe resulting residue was dissolved in ethyl acetate
  3. washwashed with 5% aq. potassium carbonate solution, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe dried solution was concentrated under vacuum

Sources & evidence

ORD record
ord-f0212d1ea4f44834a95962e49940a1b9
Source dataset
uspto-grants-2008_09
Patent number
US07419967B2

Reaction notes

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