Glycolic Acid → HCID 25069533, compound

HRID 2047315Notes

Reaction equation

HRID 2047315 reaction equation
[NH2:1][CH2:2][C@@H:3]([OH:32])[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]([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[CH:19]=3)[O:15][N:14]=2)=[CH:8][C:7]=1[CH2:30][CH3:31].[C:33](O)(=[O:36])[CH2:34][OH:35].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C([O-])(O)=O.[Na+]>[CH2:28]([N:25]([CH2:26][CH3:27])[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][C@H:3]([OH:32])[CH2:2][NH:1][C:34](=[O:35])[CH2:33][OH:36])=[C:7]([CH2:30][CH3:31])[CH:8]=3)[N:17]=2)[CH:23]=[C:22]([CH3:24])[N:21]=1)[CH3:29]

Participants

6

Reactant 4

HCID 757Glycolic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68578193HCID 68578193, compound

Product 1

HCID 25069533HCID 25069533, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (R)-1-amino-3-{4-[5-(2-diethylamino-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propan-2-ol (310 mg, 0.705 mmol), glycolic acid (59 mg, 0.776 mmol) and HOBt (114 mg, 0.846 mmol), EDC hydrochloride (149 mg, 0.776 mmol) is added. The mixture is stirred at rt for 1 h before it is diluted with sat. aq. NaHCO3 and extracted twice with EA. The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified on prep. TLC plates with DCM containing 12% of methanol to give N-(3-{4-[5-(2-diethylamino-6-methyl-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-(R)-2-hydroxy-propyl)-2-hydroxy-acetamide (296 mg) as an off-white powder; LC-MS: tR=0.78 min; [M+1]+=498.19.

Workup

  1. extractionextracted twice with EA
  2. dry with materialextracts are dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified on prep

Sources & evidence

ORD record
ord-21ccf9c8acf4426989c524cd5d4e91d6
Source dataset
uspto-grants-2013_11
Patent number
US08592460B2

Reaction notes

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