Formic Acid → HCID 16660274, compound

HRID 1360641Notes

Reaction equation

HRID 1360641 reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.[Cl:11][C:12]1[CH:21]=[C:20]2[C:15]([CH2:16][CH2:17][N:18]([S:22]([CH2:25][C@@H:26]([C@H:29]3[CH2:33][CH2:32][CH2:31][O:30]3)[NH:27][OH:28])(=[O:24])=[O:23])[CH2:19]2)=[CH:14][CH:13]=1>C1COCC1>[Cl:11][C:12]1[CH:21]=[C:20]2[C:15]([CH2:16][CH2:17][N:18]([S:22]([CH2:25][C@H:26]([N:27]([OH:28])[CH:1]=[O:3])[C@H:29]3[CH2:33][CH2:32][CH2:31][O:30]3)(=[O:23])=[O:24])[CH2:19]2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 57855487HCID 57855487, compound

Product 1

HCID 16660274HCID 16660274, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of formic acid (0.5 ml) and acetic anhydride (0.125 ml) was stirred at 0° C. for 1 hour, then a solution of (1R)-2-[(7-chloro-3,4-dihydroisoquinolin-2(1H)-yl)sulfonyl]-N-hydroxy-1-[(2R)-tetrahydrofuran-2-yl]ethanamine (80 mg, 0.22 mmol) in anhydrous THF (5 ml) was added and the resulting mixture was stirred at RT for 1 hour. The mixture was evaporated under reduced pressure. The residue was taken up with MeOH (5 ml) and heated at 55° C. for 1 hour. The reaction mixture was evaporated under reduced pressure. After purification by crystallization in EtOAc/pentane, the title compound (22) was obtained as a white powder (37 mg, 43%). HPLC, Rt: 3.0 min (purity: 94.1%). LC/MS, M+(ESI): 389.3, M−(ESI): 387.3.

Workup

  1. stirringthe resulting mixture was stirred at RT for 1 hour
  2. customThe mixture was evaporated under reduced pressure
  3. temperatureheated at 55° C. for 1 hour
  4. customThe reaction mixture was evaporated under reduced pressure
  5. customAfter purification
  6. customby crystallization in EtOAc/pentane

Sources & evidence

ORD record
ord-4606c981af584fab851bced7f75c42f7
Source dataset
uspto-grants-2011_02
Patent number
US07879876B2

Reaction notes

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