Methyl chloroformate → {3-[6-Benzyloxy-7-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-naphthalen-2-yl]-benzyl}-carbamic acid methyl ester

HRID 643889Notes

Reaction equation

HRID 643889 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:18]=[C:17]3[C:12]([CH:13]=[C:14]([O:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:15]([N:19]4[S:23](=[O:25])(=[O:24])[NH:22][C:21](=[O:26])[CH2:20]4)=[CH:16]3)=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.Cl[C:43]([O:45][CH3:46])=[O:44]>C1COCC1>[CH3:46][O:45][C:43](=[O:44])[NH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]3[C:17](=[CH:16][C:15]([N:19]4[CH2:20][C:21](=[O:26])[NH:22][S:23]4(=[O:25])=[O:24])=[C:14]([O:27][CH2:28][C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)[CH:13]=3)[CH:18]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 667509055-[7-(3-Aminomethylphenyl)-3-benzyloxynaphthalen-2-yl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one

Product 1

HCID 66750635{3-[6-Benzyloxy-7-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-naphthalen-2-yl]-benzyl}-carbamic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 5-[7-(3-aminomethylphenyl)-3-benzyloxynaphthalen-2-yl]-1,1-dioxo-1,2,5-thiadiazolidin-3-one (0.046 g, 0.097 mmol) and triethylamine (0.014 mL, 0.098 mmol) in THF (3 mL) at 0° C. is added methyl chloroformate (0.008 mL, 0.104 mmol). The reaction is stirred for 30 min and then quenched with water and extracted with CH2Cl2 (3×25 mL). The organic layers are combined and concentrated. The residue is purified via Biotage Sp1 eluting with 5-60% CH3CN/H2O to afford {3-[6-benzyloxy-7-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-naphthalen-2-yl]-benzyl}-carbamic acid methyl ester: (M−H)−=530.

Workup

  1. customquenched with water
  2. extractionextracted with CH2Cl2 (3×25 mL)
  3. concentrationconcentrated
  4. customThe residue is purified via Biotage Sp1
  5. washeluting with 5-60% CH3CN/H2O

Sources & evidence

ORD record
ord-2466b94b35a1430b87af67430b0620b3
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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