Trifluoroacetic acid → (S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(2-((5-(hydroxymethyl)thiazol-2-yl)amino)acetamido)propanoate

HRID 1755486Notes

Reaction equation

HRID 1755486 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][NH:15][C:16](=[O:26])[CH2:17][NH:18][C:19]1[S:20][C:21]([CH:24]=[O:25])=[CH:22][N:23]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].FC(F)(F)C(O)=O>CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][NH:15][C:16](=[O:26])[CH2:17][NH:18][C:19]1[S:20][C:21]([CH2:24][OH:25])=[CH:22][N:23]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 86700128(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(2-((5-formylthiazol-2-yl)amino)acetamido)propanoate

Product 1

HCID 86700129(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(2-((5-(hydroxymethyl)thiazol-2-yl)amino)acetamido)propanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of material from Example 106 (10 mg, 0.026 mmol) in methanol (1.5 mL) is added sodium borohydride (3.5 mg, 0.093 mmol). The reaction is allowed to stir at room temp for 1 min, cooled to 0° C., quenched with trifluoroacetic acid (26.5 μL, 0.344 mmol) and the solvent removed in vacuo. The resulting residue is used immediately in the next reaction. LC/MS (Condition A): ret, T=2.54 min, (M+Na) 411.

Workup

  1. temperaturecooled to 0° C.
  2. customthe solvent removed in vacuo
  3. customThe resulting residue is used immediately in the next reaction
  4. customT=2.54 min, (M+Na) 411

Sources & evidence

ORD record
ord-b48bfcec8b564ee1897bd790d5340fb8
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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