Methanol → HCID 57943174, compound

HRID 1046592Notes

Reaction equation

HRID 1046592 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:7]([NH:9][C@H:10]([C:23]1[N:24]=[C:25]([CH2:28][CH3:29])[S:26][CH:27]=1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18]S(=O)(=O)O)=[CH:14][CH:13]=1)=[O:8])=[O:4].[NH4+].[OH-:38].C[OH:40]>[Pd]>[CH2:28]([C:25]1[S:26][CH:27]=[C:23]([C@@H:10]([NH:9][C:7](=[O:8])[C@@H:6]([NH:5][C:3](=[O:4])[O:2][CH3:1])[CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:40])=[O:38])=[CH:14][CH:13]=2)[N:24]=1)[CH3:29]

Participants

5

Reactant 3

HCID 887MethanolHCID 14923Ammonium HydroxideHCID 57497737HCID 57497737, compound

Product 1

HCID 57943174HCID 57943174, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Preparation of 4-((S)-2-(S)-2-(methoxycarbonylamino)-3-phenylpropanamido)-2-(2-ethylthiazol-4-yl)ethyl)phenylsulfamic acid ammonium salt (13): tert-Butyl (S)-1-(S)-2-(4-nitrophenyl)-1-(2-ethylthiazole-4-yl)ethylamino-1-oxo-3-phenylpropan-2-ylcarbamate, 12, (0.300 g) is dissolved in MeOH (4 mL). A catalytic amount of Pd/C (10% w/w) is added and the mixture is stirred under a hydrogen atmosphere 18 hours. The reaction mixture is filtered through a bed of CELITE™ and the solvent is removed under reduced pressure. The crude product is dissolved in pyridine (12 mL) and treated with SO3-pyridine (223 mg, 1.40 mmol). The reaction is stirred at room temperature for 5 minutes after which a 7% solution of NH4OH (12 mL) is added. The mixture is then concentrated and the resulting residue is purified by reverse phase chromatography to afford 25 mg of the desired product as the ammonium salt. 1H NMR (300 MHz, MeOH-d4) δ 7.14-7.24 (m, 6H), 6.97-7.0 (m, 4H), 6.62 (s, 1H), 5.10-5.30 (m, 1H), 4.36 (t, J=7.2 Hz, 1H), 3.63 (s, 3H), 3.14 (dd, J=13.5 and 6.3 Hz, 1H), 2.93-3.07 (m, 5H), 2.81 (dd, J=13.5 and 6.3 HZ, 1H), 1.39 (t, J=7.8 Hz, 3H).

Workup

  1. filtrationThe reaction mixture is filtered through a bed of CELITE™
  2. customthe solvent is removed under reduced pressure
  3. dissolutionThe crude product is dissolved in pyridine (12 mL)
  4. additionis added
  5. concentrationThe mixture is then concentrated
  6. customthe resulting residue is purified by reverse phase chromatography

Sources & evidence

ORD record
ord-a3d14cd30ca748b088caea80862725e5
Source dataset
uspto-grants-2013_10
Patent number
US08569348B2

Reaction notes

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