Acetic Acid → HCID 21048993, compound

HRID 2212374Notes

Reaction equation

HRID 2212374 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:23]3[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=3[F:30])[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][S:19]([NH2:22])(=[O:21])=[O:20])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.CN(C1C=CC=CN=1)C.[C:52](O)(=[O:54])[CH3:53]>ClCCl.C(OCC)(=O)C>[C:52]([NH:22][S:19]([CH2:18][CH2:17][CH:14]1[CH2:13][CH2:12][C:11]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:9])=[O:10])([C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[F:30])[CH2:16][CH2:15]1)(=[O:21])=[O:20])(=[O:54])[CH3:53]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21048968HCID 21048968, compound

Product 1

HCID 21048993HCID 21048993, compoundYield 61.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the product of Example 105 (141 mg, 0.28 mmol) in dichloromethane (10 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (104 mg, 0.54 mmol), dimethylaminopyridine (66 mg, 0.57 mmol) and acetic acid (0.035 mL, 0.58 mmol). The mixture was stirred for 18 hours, diluted with ethyl acetate (20 mL), washed with 2N aqueous hydrochloric acid (20 mL) and brine (100 mL), dried (MgSO4) and evaporated to leave a residue which was purified by column chromatography on silica eluting with ethyl acetate: dichloromethane:iso-hexane 2:1:1, to afford the desired product (90 mg).

Workup

  1. washwashed with 2N aqueous hydrochloric acid (20 mL) and brine (100 mL)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customto leave a residue which
  5. customwas purified by column chromatography on silica eluting with ethyl acetate: dichloromethane:iso-hexane 2:1:1

Sources & evidence

ORD record
ord-ab647239cfb6428c816aefa4d7a61403
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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