Methanol → HCID 10127250, compound

HRID 1816436Notes

Reaction equation

[O:1]=[S:2]1(=[O:27])[CH:7]=[CH:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20]C(=O)C(F)F)[O:16][C:15]3=[O:26])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[Cl:28][CH:29]([Cl:35])C(OCC)=O.C(N(CC)CC)C.[CH3:43][OH:44]>>[Cl:28][CH:29]([Cl:35])[C:43]([NH:20][CH2:19][C@@H:17]1[O:16][C:15](=[O:26])[N:14]([C:11]2[CH:12]=[CH:13][C:8]([CH:5]3[CH:6]=[CH:7][S:2](=[O:27])(=[O:1])[CH2:3][CH2:4]3)=[CH:9][CH:10]=2)[CH2:18]1)=[O:44]

Participants

Reactant 4

HCID 887Methanol

HCID 8471Triethylamine

HCID 10808Ethyl dichloroacetate

HCID 10216150HCID 10216150, compound

Product 1

HCID 10127250HCID 10127250, compoundYield 75%

Procedure

The crude amine hydrochloride prepared in Step 1 of Example 15 (0.350 g, 0.975 mmol), ethyl dichloroacetate (0.60 ml, 4.88 mmol), and triethylamine (0.27 ml, 1.95 mmol) in methanol (5 mL) are stirred at r.t. overnight. The reaction mixture is evaporated to dryness and the residue purified by PTLC (10% methanol/dichloromethane) to give the title compound as white solid (0.32 g, 75%). M.p. 159-61° C.

Workup

customThe reaction mixture is evaporated to dryness
customthe residue purified by PTLC (10% methanol/dichloromethane)

Sources & evidence

ORD record: ord-045c2f873d0443f691f3e271c4c60ae5
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06884813B2

Reaction notes

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