2-Mercaptobenzoic Acid → HCID 86657456, compound

HRID 1408838Notes

Reaction equation

HRID 1408838 reaction equation
C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([NH:34][C:35]1([CH2:51][O:52][N:53]([CH3:61])[C:54](=[O:60])[O:55][C:56]([CH3:59])([CH3:58])[CH3:57])[C:49]2[C:44](=[CH:45][CH:46]=[C:47]([Br:50])[CH:48]=2)[O:43][C:37]2([CH2:42][CH2:41][CH2:40][O:39][CH2:38]2)[CH2:36]1)C=C.C(O)(=O)C1C(=CC=CC=1)S>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH2:34][C:35]1([CH2:51][O:52][N:53]([CH3:61])[C:54](=[O:60])[O:55][C:56]([CH3:57])([CH3:58])[CH3:59])[C:49]2[C:44](=[CH:45][CH:46]=[C:47]([Br:50])[CH:48]=2)[O:43][C:37]2([CH2:42][CH2:41][CH2:40][O:39][CH2:38]2)[CH2:36]1

Participants

6

Reactant 3

HCID 54432-Mercaptobenzoic AcidHCID 821241,4-Bis(diphenylphosphino)butaneHCID 86657457HCID 86657457, compound

Product 1

HCID 86657456HCID 86657456, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Pd2(dba)3 (7.6 mg, 0.038 mmol) and 1,4-bis(diphenylphosphino)butane (3.6 mg, 0.038 mmol) in THF (3 mL) under N2 atmosphere was stirred for 15 min. Then the solution was added to a solution of tert-butyl (4-(allylamino)-6-bromo-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-yl)methoxy(methyl)carbamate produced in previous step in THF (3 mL), followed by thiosalicylic acid (14 mg, 0.91 mmol). The mixture was stirred for 16 h. The solvent was removed under reduced pressure. The residue was purified by preparative HPLC to recover 28 mg of starting material as TFA salt and 10 mg of the desired product as TFA salt. MS ESI+ve m/z 457 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was purified by preparative HPLC
  3. customto recover 28 mg of starting material as TFA salt and 10 mg of the desired product as TFA salt

Sources & evidence

ORD record
ord-5d3579deb8784fd1b852376cff283eba
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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