Hydrochloric Acid → HCID 131721343, compound

HRID 1585743Notes

Reaction equation

HRID 1585743 reaction equation
O.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]([CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][C:28]([O:37][CH2:38][CH2:39][OH:40])([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:27][CH2:26]2)[CH2:12][N:13]([CH3:22])[C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:7]=[CH:8][C:9]=1[Cl:10].C(N(CC)CC)C.[C:48]([Cl:51])(=[O:50])[CH3:49].Cl>C(Cl)Cl>[OH2:21].[ClH:3].[C:48]([O:40][CH2:39][CH2:38][O:37][C:28]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:27][CH2:26][N:25]([CH2:24][CH2:23][CH:11]([C:6]2[CH:7]=[CH:8][C:9]([Cl:10])=[C:4]([Cl:3])[CH:5]=2)[CH2:12][N:13]([CH3:22])[C:14](=[O:21])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:30][CH2:29]1)(=[O:50])[CH3:49].[C:48]([O:40][CH2:39][CH2:38][O:37][C:28]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:27][CH2:26][N:25]([CH2:24][CH2:23][CH:11]([C:6]2[CH:7]=[CH:8][C:9]([Cl:10])=[C:4]([Cl:3])[CH:5]=2)[CH2:12][N:13]([CH3:22])[C:14](=[O:21])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:30][CH2:29]1)(=[O:50])[CH3:49].[ClH:51]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21840059HCID 21840059, compound

Product 1

HCID 131721343HCID 131721343, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.6 g of the compound obtained in EXAMPLE 1 and 0.3 ml of triethylamine in 20 ml of DCM is cooled to 0-5° C., 0.08 ml of acetyl chloride is added and the mixture is left stirring while the temperature is allowed to rise to RT. The reaction mixture is concentrated under vacuum and the residue is chromatographed on silica, eluting with DCM and then with a DCM/MeOH (97:3; v/v) mixture. The product obtained is dissolved in DCM, the mixture is acidified to pH 1 by adding ethereal hydrogen chloride and the precipitate formed is drained. 0.23 g of the expected product is obtained, m.p.=95° C. ##STR45##

Workup

  1. waitthe mixture is left
  2. customto rise to RT
  3. concentrationThe reaction mixture is concentrated under vacuum
  4. customthe residue is chromatographed on silica
  5. washeluting with DCM
  6. customThe product obtained
  7. customthe precipitate formed

Sources & evidence

ORD record
ord-ec69865a1ea045849d8ccade6d345c64
Source dataset
uspto-grants-1999_08
Patent number
US05939411

Reaction notes

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