HCID 86745736, compound → HCID 18639814, compound

HRID 1031253Notes

Reaction equation

HRID 1031253 reaction equation
[C:1]([S:4][CH:5]([CH:18]([C:23]([NH:25][C@H:26]([C:36]([NH:38][CH3:39])=[O:37])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1)=[O:24])[CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:6][C:7]([NH:9][CH2:10][C:11]([O:13]C(C)(C)C)=[O:12])=[O:8])(=[O:3])[CH3:2]>FC(F)(F)C(O)=O.O>[C:1]([S:4][CH:5]([CH:18]([C:23]([NH:25][C@H:26]([C:36]([NH:38][CH3:39])=[O:37])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1)=[O:24])[CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:6][C:7]([NH:9][CH2:10][C:11]([OH:13])=[O:12])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86745736HCID 86745736, compound

Product 1

HCID 18639814HCID 18639814, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-[3-acetylmercapto-6-methyl-4-[[[1-(S)-[(methylamino)carbonyl]-2-(4-methoxyphenyl)ethyl]amino]carbonyl]heptanoylamino]ethanoic acid, t-butyl ester (E12, Isomer A; 60 mg, 0.11 mmol) in trifluoroacetic acid (1.5 ml) and water (0.05 ml) was stirred in an ice bath for 1 h, then at room temperature for 2 h. The solvent was evaporated in vacuo and the residue was azeotroped dry with toluene to leave the title compound as a single isomer (Isomer A), mp 188°-192° C.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was azeotroped
  3. dry with materialdry with toluene

Sources & evidence

ORD record
ord-74a45c725bbe4386bcdaf9c13b0a6ad7
Source dataset
uspto-grants-1992_04
Patent number
US05109000

Reaction notes

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