Phenylmethyl (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoyl)-3-({[4-(2-pyridinyl)-2-pyrimidinyl]amino}carbonyl)-1-pyrazolidinecarboxylate → Phenylmethyl (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-3-({[4-(2-pyridinyl)-2-pyrimidinyl]amino}carbonyl)-1-pyrazolidinecarboxylate

HRID 1396964Notes

Reaction equation

HRID 1396964 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:40][N:41]([CH:49]=[O:50])[O:42]C2CCCCO2)[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[N:23]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[CH:21]=[CH:20][N:19]=3)=[O:16])[CH2:13][CH2:12][N:11]2[C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1>CC(O)=O.O>[CH:1]1([CH2:6][C@H:7]([CH2:40][N:41]([CH:49]=[O:50])[OH:42])[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[N:23]=[C:22]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[CH:21]=[CH:20][N:19]=3)=[O:16])[CH2:13][CH2:12][N:11]2[C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 131732107Phenylmethyl (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoyl)-3-({[4-(2-pyridinyl)-2-pyrimidinyl]amino}carbonyl)-1-pyrazolidinecarboxylate

Product 1

HCID 131732109Phenylmethyl (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)-3-({[4-(2-pyridinyl)-2-pyrimidinyl]amino}carbonyl)-1-pyrazolidinecarboxylateYield 9.1%

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Procedure

A solution of phenylmethyl (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoyl)-3-({[4-(2-pyridinyl)-2-pyrimidinyl]amino}carbonyl)-1-pyrazolidinecarboxylate in AcOH/water (5 mL, 4:1) was stirred at rt for 48 h. The solvents were removed under vacuum and the residue was purified by RP-HPLC to provide the title compound (32 mg, 9.1%) as light-yellow gum.

Workup

  1. customThe solvents were removed under vacuum
  2. customthe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-51a8699dbdd14ac782fe40c5fa6445ac
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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