Methoxyacetyl chloride → HCID 90387045, compound

HRID 508401Notes

Reaction equation

HRID 508401 reaction equation
[CH3:1][O:2][CH2:3][C:4](Cl)=[O:5].[NH2:7][C@H:8]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)=[CH:20][CH:19]=1)[CH2:9][C@:10]([CH2:15][OH:16])([CH3:14])[C:11]([OH:13])=[O:12]>C(Cl)Cl.CCN(CC)CC>[Cl:30][C:26]1[CH:25]=[C:24]([C:21]2[CH:20]=[CH:19][C:18]([CH2:17][C@@H:8]([NH:7][C:4](=[O:5])[CH2:3][O:2][CH3:1])[CH2:9][C@:10]([CH2:15][OH:16])([CH3:14])[C:11]([OH:13])=[O:12])=[CH:23][CH:22]=2)[CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 89964569HCID 89964569, compound

Product 1

HCID 90387045HCID 90387045, compoundYield 16.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

Methoxy-acetyl chloride (7 mg, 30 μmol) was combined with a 0.4 mL solution of 0.075 M of (2S,4R)-4-amino-5-(3′-chlorobiphenyl-4-yl)-2-hydroxymethyl-2-methyl-pentanoic acid (136 mg, 30 μmol) in DCM and Et3N (110 μL). The resulting mixture was stirred for 10 minutes. The solvent was evaporated and the residue was dissolved in AcOH and purified by preparative HPLC to yield the title compound (2.1 mg). MS m/z [M+H]+ calc'd for C22H26ClNO5, 420.15. found 420.2.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in AcOH
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-96374bf3b602465cb7b952e0b23aeb0c
Source dataset
uspto-grants-2015_08
Patent number
US09096496B2

Reaction notes

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