Methanol → 7-(4-((1,2,3,4-Tetrahydronaphthalen-2-yl)carbamoyl)phenoxy)-6-cyanochroman-4-carboxylic acid

HRID 1021450Notes

Reaction equation

HRID 1021450 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[NH:11][C:12]([C:14]1[CH:36]=[CH:35][C:17]([O:18][C:19]2[CH:28]=[C:27]3[C:22]([CH:23]([C:29]([O:31]C)=[O:30])[CH2:24][CH2:25][O:26]3)=[CH:21][C:20]=2[C:33]#[N:34])=[CH:16][CH:15]=1)=[O:13].[OH-].[Na+].CO>C1COCC1.C(OCC)(=O)C.Cl>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[NH:11][C:12]([C:14]1[CH:36]=[CH:35][C:17]([O:18][C:19]2[CH:28]=[C:27]3[C:22]([CH:23]([C:29]([OH:31])=[O:30])[CH2:24][CH2:25][O:26]3)=[CH:21][C:20]=2[C:33]#[N:34])=[CH:16][CH:15]=1)=[O:13]

Participants

7

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67081013Methyl 7-(4-((1,2,3,4-tetrahydronaphthalen-2-yl)carbamoyl)phenoxy)-6-cyanochroman-4-carboxylate

Product 1

HCID 445999227-(4-((1,2,3,4-Tetrahydronaphthalen-2-yl)carbamoyl)phenoxy)-6-cyanochroman-4-carboxylic acidYield 31%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 7-(4-((1,2,3,4-tetrahydronaphthalen-2-yl)carbamoyl)phenoxy)-6-cyanochroman-4-carboxylate (10 mg, 0.021 mmol) was diluted with THF (500 μL) followed by the addition of NaOH (0.12 ml, 0.12 mmol) and methanol (100 μL). After stirring for 1 hour, the reaction was diluted with ethyl acetate and 2N HCl. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated to yield 7-(4-((1,2,3,4-tetrahydronaphthalen-2-yl)carbamoyl)phenoxy)-6-cyanochroman-4-carboxylic acid (3.0 mg, 31% yield). MS (ESI)=469.0 (M+H).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c06838a98f364298a1dc0ae5566485ea
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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