Water → HCID 86752944, compound

HRID 1957579Notes

Reaction equation

HRID 1957579 reaction equation
C[O:2][C:3](=[O:39])[C@@H:4]([NH:31][S:32]([CH2:35][CH2:36][CH2:37][CH3:38])(=[O:34])=[O:33])[CH2:5][NH:6][C:7]([C:9]1[O:13][N:12]=[C:11]([O:14][CH2:15][CH2:16][CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)[CH:10]=1)=[O:8].O[Li].O.O.OS([O-])(=O)=O.[Na+]>C1COCC1>[C:24]([N:21]1[CH2:20][CH2:19][CH:18]([CH2:17][CH2:16][CH2:15][O:14][C:11]2[CH:10]=[C:9]([C:7]([NH:6][CH2:5][C@H:4]([NH:31][S:32]([CH2:35][CH2:36][CH2:37][CH3:38])(=[O:34])=[O:33])[C:3]([OH:39])=[O:2])=[O:8])[O:13][N:12]=2)[CH2:23][CH2:22]1)([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 516919Sodium BisulfateHCID 86752943HCID 86752943, compound

Product 1

HCID 86752944HCID 86752944, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-8 (1.86 mg, 0.32 mmol), LiOH.H2O (67 mg, 1.6 mmol), H2O (2 mL), and THF (8 mL) was stirred at ambient temperature for 1.0 h. The solution was acidified with 1M NaHSO4 followed by evaporation of THF. The residue was partitioned between EtOAc and brine. The EtOAc layer was then dried (MgSO4) and concentrated to give 3-9 as a pale yellow solid. Rf 0.40 (silica, 9/.0.5/0.5 CH2Cl2 :CH3OH:HOAc).

Workup

  1. customfollowed by evaporation of THF
  2. customThe residue was partitioned between EtOAc and brine
  3. dry with materialThe EtOAc layer was then dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-64da6f58d0bf45ea8ee01a8bf3c0e615
Source dataset
uspto-grants-1998_07
Patent number
US05786373

Reaction notes

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