Hydrochloric Acid → HCID 18512362, compound

HRID 1370933Notes

Reaction equation

HRID 1370933 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:41]=[CH:40][C:25]([O:26][C:27]2[CH:39]=[CH:38][C:30]([O:31][CH2:32][CH2:33][CH2:34][C:35](O)=[O:36])=[CH:29][CH:28]=2)=[CH:24][CH:23]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[C:10]=1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.Cl.[CH3:66][O:67][C:68](=[O:71])[CH2:69][NH2:70].C(N(CC)C(C)C)(C)C.Cl>CN(C)C=O>[CH2:1]([N:8]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:26][C:27]2[CH:28]=[CH:29][C:30]([O:31][CH2:32][CH2:33][CH2:34][C:35]([NH:70][CH2:69][C:68]([O:67][CH3:66])=[O:71])=[O:36])=[CH:38][CH:39]=2)=[CH:40][CH:41]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][S:16]([CH3:19])(=[O:17])=[O:18])[C:10]=1[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 18512383HCID 18512383, compound

Product 1

HCID 18512362HCID 18512362, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The product from Example 233 (28.7 mg, 0.05 mmoles) in anhydrous dimethylformamide (0.5 ml) was treated with 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (14 mg, 0.07 mmoles) and 1-hydroxybenzotriazole hydrate (10 mg, 0.07 mmoles) at room temperature for 15 minutes. A mixture of glycine methyl ester hydrochloride (12.6 mg, 0.1 mmole) and N,N-diisopropylethylamine (0.014 ml, 0.1 mmole) in anhydrous dimethylformamide (0.235 ml) was added to the reaction and shaken at room temperature overnight. The reacton mixture was acidified with 1N aqueous hydrochloric acid and extracted with dichloromethane. The organic layer was washed with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, filtered and filtrate concentrated in vacuo. The residue purified by HPLC to provide the titled compound.

Workup

  1. additionwas added to the reaction
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationfiltrate concentrated in vacuo
  7. customThe residue purified by HPLC

Sources & evidence

ORD record
ord-7806d060a2cc4a5e897918a06de19efe
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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