Hydrochloric Acid → HCID 136337784, compound

HRID 533223Notes

Reaction equation

HRID 533223 reaction equation
CC1(C)[O:6][C@H:5]([C@@H:7]([NH:11][CH2:12][C:13]2[C:17]3[N:18]=[CH:19][NH:20][C:21](=[O:22])[C:16]=3[NH:15][CH:14]=2)[CH2:8][S:9][CH3:10])[CH2:4][O:3]1.Cl>CO>[OH:6][C@@H:5]([CH2:4][OH:3])[C@@H:7]([NH:11][CH2:12][C:13]1[C:17]2[N:18]=[CH:19][NH:20][C:21](=[O:22])[C:16]=2[NH:15][CH:14]=1)[CH2:8][S:9][CH3:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 136337785HCID 136337785, compound

Product 1

HCID 136337784HCID 136337784, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Example 27.6 (0.049 g, 0.15 mmol) was stirred in a 1% hydrogen chloride solution in methanol (10 ml) for 3 h at ambient temperature. The reaction mixture was neutralised with Amberlyst A-21 ion exchange resin. The resin was filtered and the reaction solution concentrated. The residue was chromatographed (methanol [3,5N ammonia solution]-DCM, 1:4) giving a white solid (0.036 g, 83%). 1H NMR revealed this compound to be identical to the enantiomer from Example 26.7. +ESMS Found 299.1180 (M+H)+ C12H19N4O3S requires 299.1178.

Workup

  1. filtrationThe resin was filtered
  2. concentrationthe reaction solution concentrated
  3. customThe residue was chromatographed (methanol [3,5N ammonia solution]-DCM, 1:4)

Sources & evidence

ORD record
ord-a0bf3d68a80e4ceabafd4a94924e642a
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

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