Glycolic Acid → HCID 57437439, compound

HRID 1665970Notes

Reaction equation

HRID 1665970 reaction equation
[C:1](O)(=[O:4])[CH2:2][OH:3].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[NH2:37][CH2:38][CH:39]([OH:64])[CH2:40][O:41][C:42]1[CH:47]=[CH:46][C:45]([CH2:48][CH2:49][C:50]([C:52]2[S:53][C:54]([CH3:63])=[C:55]3[CH2:60][C:59]([CH3:62])([CH3:61])[CH2:58][CH2:57][C:56]=23)=[O:51])=[CH:44][CH:43]=1>C(Cl)Cl>[OH:4][CH2:1][C:2]([NH:37][CH2:38][CH:39]([OH:64])[CH2:40][O:41][C:42]1[CH:43]=[CH:44][C:45]([CH2:48][CH2:49][C:50](=[O:51])[C:52]2[S:53][C:54]([CH3:63])=[C:55]3[CH2:60][C:59]([CH3:61])([CH3:62])[CH2:58][CH2:57][C:56]=23)=[CH:46][CH:47]=1)=[O:3]

Participants

6

Reactant 4

HCID 757Glycolic Acid2×HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate2×HCID 57508928HCID 57508928, compound

Product 1

HCID 57437439HCID 57437439, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of glycolic acid (1.5 eq.) in DCM (10 mL), TBTU (1.3 eq.) and DIPEA (4.0 eq.) is added. The mixture is stirred at rt for 10 min before the appropriate 3-[4-(3-amino-2-hydroxy-propoxy)-phenyl]-1-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propan-1-one (0.5-1.0 mmol, 1. eq.) is added. Stirring is continued at rt for 1 h before another portion of glycolic acid (0.7 eq.) and TBTU (0.6 eq.) is added. The mixture is stirred for another hour, is diluted with DCM and washed with sat. aq. NaHCO3 solution. The wash solutions are extracted back with DCM. The combined organic extracts are dried over MgSO4, filtered and the solvent is evaporated. The crude product is purified by chromatography on prep. TLC plates using DCM containing 5% of methanol to give the desired 2-hydroxy-N-(2-hydroxy-3-{4-[3-oxo-3-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propyl]-phenoxy}-propyl)-acetamide as an almost colourless foam.

Workup

  1. additionis added
  2. additionis added
  3. stirringThe mixture is stirred for another hour
  4. washwashed with sat. aq. NaHCO3 solution
  5. extractionThe wash solutions are extracted back with DCM
  6. dry with materialThe combined organic extracts are dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent is evaporated
  9. customThe crude product is purified by chromatography on prep

Sources & evidence

ORD record
ord-e9fb26fbba2648ecb9b172e7932cb5a6
Source dataset
uspto-grants-2011_10
Patent number
US08039644B2

Reaction notes

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