Glycolic Acid → HCID 24752897, compound

HRID 2040813Notes

Reaction equation

HRID 2040813 reaction equation
[NH2:1][CH2:2][CH:3]([OH:27])[CH2:4][O:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([C:13]2[N:17]=[C:16]([C:18]3[CH:23]=[C:22]([CH3:24])[N:21]=[C:20]([Cl:25])[CH:19]=3)[O:15][N:14]=2)=[CH:8][C:7]=1[CH3:26].[C:28](O)(=[O:31])[CH2:29][OH:30].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl.CC(=O)OCC>[Cl:25][C:20]1[CH:19]=[C:18]([C:16]2[O:15][N:14]=[C:13]([C:9]3[CH:10]=[C:11]([CH3:12])[C:6]([O:5][CH2:4][CH:3]([OH:27])[CH2:2][NH:1][C:29](=[O:30])[CH2:28][OH:31])=[C:7]([CH3:26])[CH:8]=3)[N:17]=2)[CH:23]=[C:22]([CH3:24])[N:21]=1

Participants

7

Reactant 4

HCID 757Glycolic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59234767HCID 59234767, compound

Product 1

HCID 24752897HCID 24752897, compoundYield 14.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (RS)-1-amino-3-{4-[5-(2-chloro-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-propan-2-ol (134 mg, 0.345 mmol) in DCM (10 mL), glycolic acid (54 mg, 0.707 mmol) and DIPEA (132 mg, 1.02 mmol) is added. The mixture is cooled to 0° C. and TBTU (134 mg, 0.416 mmol) is added. The mixture is stirred at 0° C. for 1 h, then at rt for 16 h before it is diluted with EA (250 mL), washed with 1 N aq. NaOH solution (3×25 mL), 1 N aq. KHSO4 (25 mL) and brine (25 mL), dried over Na2SO4, filtered and concentrated. The crude product is purified by prep. HPLC to give N-((RS)-3-{4-[5-(2-chloro-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-2-hydroxy-propyl)-2-hydroxy-acetamide (23 mg) as a colourless resin; LC-MS: tR=0.91 min, [M+1]+=447.44.

Workup

  1. washwashed with 1 N aq. NaOH solution (3×25 mL), 1 N aq. KHSO4 (25 mL) and brine (25 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by prep

Sources & evidence

ORD record
ord-44d384875fd349df80d46146e6a8978a
Source dataset
uspto-grants-2013_11
Patent number
US08580824B2

Reaction notes

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