Methanol → 2-(4-(N-(tert-butoxycarbonyl)methylsulfonamido)-3-(cyclopropylmethoxy)-benzoyloxy)acetic acid

HRID 1776515Notes

Reaction equation

HRID 1776515 reaction equation
[C:1]([O:5][C:6]([N:8]([C:13]1[CH:32]=[CH:31][C:16]([C:17]([O:19][CH2:20][C:21]([O:23]CC2C=CC=CC=2)=[O:22])=[O:18])=[CH:15][C:14]=1[O:33][CH2:34][CH:35]1[CH2:37][CH2:36]1)[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO>CCOC(C)=O.[Pd]>[C:1]([O:5][C:6]([N:8]([C:13]1[CH:32]=[CH:31][C:16]([C:17]([O:19][CH2:20][C:21]([OH:23])=[O:22])=[O:18])=[CH:15][C:14]=1[O:33][CH2:34][CH:35]1[CH2:36][CH2:37]1)[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 887MethanolHCID 894599242-(benzyloxy)-2-oxoethyl 4-(N-(tert-butoxycarbonyl)methylsulfonamido)-3-(cyclopropylmethoxy)benzoate

Product 1

HCID 894599232-(4-(N-(tert-butoxycarbonyl)methylsulfonamido)-3-(cyclopropylmethoxy)-benzoyloxy)acetic acidYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-(benzyloxy)-2-oxoethyl 4-(N-(tert-butoxycarbonyl)methylsulfonamido)-3-(cyclopropylmethoxy)benzoate (2.6 g, 4.87 mmol) was suspended in EtOAc (30 ml) and MeOH (10 ml) in a 250 ml Parr bottle; 10% Pd/C (0.176 g, 0.165 mmol) was added; and the mixture was hydrogenated at the Parr apparatus for 2 hours (H2 pressure: 30 psi), then the catalyst was filtered over a pad of celite and the solvent was evaporated to dryness; 2-(4-(N-(tert-butoxycarbonyl)methylsulfonamido)-3-(cyclopropylmethoxy)benzoyloxy)-acetic acid was obtained as a white amorphous solid (1.7 g, 3.83 mmol, 79% yield, MS/ESI+ 465.9 [MNa]+) and used as such in the following reaction without further purification.

Workup

  1. filtration(H2 pressure: 30 psi), then the catalyst was filtered over a pad of celite
  2. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-388d1136d95f4484b1ad36b76879993e
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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