Hydrochloric Acid → 4-[(1-Hydroxy-naphthalene-2-carbonyl)-amino]-tetrahydro-thiopyran-4-carboxylic acid methyl ester

HRID 1039108Notes

Reaction equation

HRID 1039108 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([OH:14])=O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)C(C)C)(C)C.Cl.[CH3:47][O:48][C:49]([C:51]1([NH2:57])[CH2:56][CH2:55][S:54][CH2:53][CH2:52]1)=[O:50].Cl>O.CN(C=O)C>[CH3:47][O:48][C:49]([C:51]1([NH:57][C:12]([C:3]2[CH:4]=[CH:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]=2[OH:1])=[O:14])[CH2:52][CH2:53][S:54][CH2:55][CH2:56]1)=[O:50]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 68441-Hydroxy-2-naphthoic acidHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22907152Methyl 4-aminothiane-4-carboxylate hydrochloride

Product 1

HCID 688438794-[(1-Hydroxy-naphthalene-2-carbonyl)-amino]-tetrahydro-thiopyran-4-carboxylic acid methyl esterYield 100.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.50 g 1-hydroxy-2-naphthoic acid in 5 ml abs. DMF under inert atmosphere 0.18 g 1-hydroxybenzotriazole, 0.71 g 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 0.7 ml N,N-diisopropylethylamine were added. After 15 minutes 0.62 g 4-amino-tetrahydro-thiopyran-4-carboxylic acid methyl ester hydrochloride, followed by 0.55 ml N,N-diisopropylethylamine were added. After 16 h at room temperature and 5 h at 60° C. the reaction was poured unto water, adjusted to pH2 with 2 M HCl and extracted with ethyl acetate twice. The combined organic layers were washed with 2M HCl, 2M aqueous sodium carbonate solution and brine. The organic layer was dried over magnesium sulphate, and concentrated to yield 0.92 g of 4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-tetrahydro-thiopyran-4-carboxylic acid methyl ester.

Workup

  1. additionwere added
  2. extractionextracted with ethyl acetate twice
  3. washThe combined organic layers were washed with 2M HCl, 2M aqueous sodium carbonate solution and brine
  4. dry with materialThe organic layer was dried over magnesium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3364820043b240b8afede4aece688fe8
Source dataset
uspto-grants-2013_10
Patent number
US08552033B2

Reaction notes

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