4-Methylmorpholine → HCID 86706383, compound

HRID 1396948Notes

Reaction equation

HRID 1396948 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:28][N:29]([CH:38]=[O:39])[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:8]([N:10]2[C@H:14](C(O)=O)[CH2:13][CH2:12][N:11]2[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.CN1CCOCC1.COC1N=[C:53]([O:55]C)[N:52]=[C:51]([N+:57]2(C)[CH2:62][CH2:61]OCC2)[N:50]=1.S(O)(O)(=O)=O.N1C=CN=C1N>C(#N)C>[CH:1]1([CH2:6][C@H:7]([CH2:28][N:29]([CH:38]=[O:39])[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:8]([N:10]2[C@H:14]([C:53]([NH:52][C:51]3[NH:50][CH:61]=[CH:62][N:57]=3)=[O:55])[CH2:13][CH2:12][N:11]2[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 135136Bis(2-amino-1H-imidazole) sulphateHCID 27340604-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-iumHCID 86706346(3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid

Product 1

HCID 86706383HCID 86706383, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid (121 mg, 0.225 mmol) in acetonitrile (4 mL) at 0° C. was added 4-methylmorpholine (0.087 mL, 0.788 mmol), followed by 4-[4,6-bis(methyloxy)-1,3,5-triazin-2-yl]-4-methylmorpholin-4-ium (DMTMM) (89 mg, 0.270 mmol). The solution was stirred for 15 min, and then 1H-imidazol-2-amine sulfate (38.7 mg, 0.293 mmol) was added. The reaction mixture was warmed up to room temperature and stirred overnight. The solvent was evaporated and the residue was purified by RP-HPLC to provide phenylmethyl (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-3-[(1H-imidazol-2-ylamino)carbonyl]-1-pyrazolidinecarboxylate as a colorless gum (39 mg, 29%)

Workup

  1. stirringstirred overnight
  2. customThe solvent was evaporated
  3. customthe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-aeb14974e2df467d8f4d09244501b132
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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