Hydrochloric Acid → HCID 136337782, compound

HRID 533219Notes

Reaction equation

HRID 533219 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][N:20]=[C:21]([OH: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 178503801HCID 178503801, compound

Product 1

HCID 136337782HCID 136337782, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Example 26.6 (0.055 g, 0.16 mmol) was stirred in a 1% hydrogen chloride solution in methanol (10 ml) for 1.5 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 (0.035 g, 72%). 1H NMR (CD3OD) δ ppm 7.98 (s, 1H), 7.60 (s, 1H), 4.44 (ABq, 2H), 3.97 (q, J=3.8 Hz, 1H), 3.76 (dd, J=11.7, 4.2 Hz, 1H), 3.67 (dd, J=11.7, 3.8 Hz, 1H), 3.44 (m, 1H), 2.92 (m, 2H), 2.08 (s, 3H). 13C NMR (CD3OD) δ 156.2, 145.6, 144.0, 130.7, 120.0, 109.8, 70.1, 66.0, 60.0, 41.4, 33.9, 16.0. +ESMS Found 299.1194: (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-ffe6a196bb14416f9b0c6eed29cdc5a2
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

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