Ninhydrin → HCID 10644173, compound

HRID 1422172Notes

Reaction equation

HRID 1422172 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:22][C:21]2[CH:23]=[C:17]([CH:18]=[CH:19][CH:20]=2)[CH2:16][C@@H:15]([C:24]([O:26]C)=[O:25])[NH:14][C:13](=[O:28])[CH2:12][NH:11][C:10]1=[O:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].C(Cl)(Cl)Cl.CO.CC(O)=O.C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O>C1COCC1.CO>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:22][C:21]2[CH:23]=[C:17]([CH:18]=[CH:19][CH:20]=2)[CH2:16][C@@H:15]([C:24]([OH:26])=[O:25])[NH:14][C:13](=[O:28])[CH2:12][NH:11][C:10]1=[O:29])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 10236NinhydrinHCID 14798Sodium HydroxideHCID 10621299HCID 10621299, compound2×HCID 21866353chloroform methanol HOAc

Product 1

HCID 10644173HCID 10644173, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Cyclic peptide ester 13 (190 mg, 0.45 mmol) was dissolved in warm THF/MeOH (40 mL) and cooled to rt. NaOH (1 N, 0.5 mL) was slowly added with stirring. After 1 h, the completed reaction (TLC-disappearance of 13, 120:2:1 CHCl3 /MeOH/AcOH, ninhydrin stain) was concentrated and the residue was dissolved in water. Dropwise addition of 2 N HCl induced precipitation of the product which was collected on a filter and dried under vacuum in a dessicator to give a white solid (140 mg, 74%). mp >250° C; 1H NMR (CDCl3 /DMSO-d6): δ 8.30 (br s, 1 H), 7.98 (t, 1 H, J=6.3 Hz), 7.23 (d, 1 H, J=9.4 Hz), 7.14 (t, 1 H, J=7.0 Hz), 6.96 (d, 1 H, J=7.0 Hz), 6.66 (s, 1 H), 6.37 (d, 1 H, J=7.8 Hz), 4.39 (m, 1 H), 4.05 (m, 1 H), 3.85 (dd, 1 H, J=8.8, 14.0 Hz), 3.27 (1 H, obscured by H2O peak), 3.02-2.78 (m, 3 H), 2.67 (dd, 1 H, 8.2 Hz, J=12.9 Hz), 1.34 (s, 9 H); 13C NMR (DMSO-d6 ; CD3OD): δ 173.27, 173.05, 169.97, 156.14, 137.34, 136.43, 133.51, 129.55, 128.80, 128.18, 80.24, 56.76, 52.70, 49.45, 44.16, 37.58, 28.73. Anal. Calcd for C19H25N3O6H2O: C, 55.74; H, 6.65; N, 10.26. Found: C, 55.16; H, 6.59; N, 9.90.

Workup

  1. concentrationwas concentrated
  2. dissolutionthe residue was dissolved in water
  3. additionDropwise addition of 2 N HCl
  4. customprecipitation of the product which
  5. customwas collected on
  6. filtrationa filter
  7. customdried under vacuum in a dessicator

Sources & evidence

ORD record
ord-d15fff5b5ea84e99811e8c70534521ad
Source dataset
uspto-grants-2000_06
Patent number
US06080838

Reaction notes

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