Hydrochloric Acid → HCID 86742659, compound

HRID 2291529Notes

Reaction equation

HRID 2291529 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][S:8][CH2:9][CH2:10][C:11]([NH:13][CH2:14][CH2:15][N:16]1[CH:20]=[C:19]([CH2:21][CH2:22][NH:23]C(OCC[Si](C)(C)C)=O)[N:18]=[CH:17]1)=[O:12].CCOC(C)=O.CO.[NH4+].[OH-].[ClH:43]>C(#N)C>[ClH:43].[ClH:43].[ClH:43].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:7][S:8][CH2:9][CH2:10][C:11]([NH:13][CH2:14][CH2:15][N:16]1[CH:20]=[C:19]([CH2:21][CH2:22][NH2:23])[N:18]=[CH:17]1)=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21901312Ethyl acetate methanol ammonium hydroxideHCID 53804869HCID 53804869, compound

Product 1

HCID 86742659HCID 86742659, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

13 mg (0.026 mmol) of IV is dissolved in 1 ml of acetonitrile containing 0.15 ml of conc. HCl. The reaction mixture is stirred at room temperature for 2.5 hours. TLC on silica gel with EtOAc--MeOH--NH4OH (80:20:1) as the mobile phase shows that the trimethylsilylethyloxycarbonyl protective group has been completely removed after 2.5 hours. The reaction solution is evaporated, whereupon an NMR analysis is run in D2O+ deuterated acetonitrile. ##STR4## 1-CH2 -imidazole 4.18 t, --CH2NHCO 3.52 t, H3N+CH2 -- 3.18 t, 4-CH2 -imidazole about 3.0 t, --CH2S-- 3.0 t, --COCH2 -- 2.57 t.

Workup

  1. customhas been completely removed after 2.5 hours
  2. customThe reaction solution is evaporated, whereupon an NMR analysis

Sources & evidence

ORD record
ord-d9918fcae17f41d7a501b34fd35d069d
Source dataset
uspto-grants-1989_01
Patent number
US04797370

Reaction notes

Loading…