2-Mercaptobenzoic Acid → HCID 86657456, compound

HRID 2096647Notes

Reaction equation

HRID 2096647 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-d051f115b7e54493a87a66a332cd9b17
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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