Glycolic Acid → HCID 59272937, compound

HRID 1666593Notes

Reaction equation

HRID 1666593 reaction equation
[NH2:1][CH2:2][CH:3]([OH:29])[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]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=3)[O:15][N:14]=2)=[CH:8][C:7]=1[CH3:28].[C:30](O)(=[O:33])[CH2:31][OH:32].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.CC(=O)OCC>[OH:33][CH2:30][C:31]([NH:1][CH2:2][CH:3]([OH:29])[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]=[CH:22][C:21]([O:24][CH:25]([CH3:26])[CH3:27])=[CH:20][CH:19]=3)[O:15][N:14]=2)=[CH:8][C:7]=1[CH3:28])=[O:32]

Participants

7

Reactant 4

HCID 757Glycolic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 59272941HCID 59272941, compound

Product 1

HCID 59272937HCID 59272937, compoundYield 20.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-amino-3-{4-[5-(4-isopropoxy-phenyl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-propan-2-ol (277 mg, 0.698 mmol), glycolic acid (80 mg, 1.05 mmol), DIPEA (362 mg, 2.80 mmol) and TBTU (382 mg, 1.19 mmol) in DMF (10 mL) is stirred at rt for 16 h before it is diluted with EA, washed with water, and concentrated. The crude product is purified by chromatography on prep. TLC plates with DCM containing 10% of methanol to give 2-hydroxy-N-(2-hydroxy-3-{4-[5-(4-isopropoxy-phenyl)-[1,2,4]oxadiazol-3-yl]-2,6-dimethyl-phenoxy}-propyl)-acetamide (64 mg) as a pale yellow solid, LC-MS: tR=0.94 min, [M+1]+=456.18, 1H NMR (D6-DMSO): δ 1.30 (d, J=5.9 Hz, 6H), 2.31 (s, 6H), 3.16-3.25 (m, 2H), 3.63-3.79 (m, 2H), 3.81 (d, J=5.6 Hz, 2H), 3.86-3.97 (m, 1H), 4.72-4.83 (m, 1H), 5.28 (d, J=5.3 Hz, 1H), 5.54 (t, J=5.9 Hz, 1H), 7.14 (d, J=9.1 Hz, 2H), 7.68 (t, J=5.6 Hz, 1H), 7.73 (s, 2H), 8.08 (d, J=9.1 Hz, 2H).

Workup

  1. washwashed with water
  2. concentrationconcentrated
  3. customThe crude product is purified by chromatography on prep

Sources & evidence

ORD record
ord-0009f9b918e145c38dfbfccb40b17b99
Source dataset
uspto-grants-2011_10
Patent number
US08044076B2

Reaction notes

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