Triethylamine → HCID 20765639, compound

HRID 984497Notes

Reaction equation

HRID 984497 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([N:20]2[CH2:31][CH2:30][C:23]3([NH:27]C(=O)N[C:24]3=[O:29])[CH2:22][CH2:21]2)=[O:19])=[C:12]([Cl:32])[C:11]=1[Cl:33].[O:34](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O.C(N(CC)CC)C.[OH-].[Na+]>COCCOC.CN(C1C=CN=CC=1)C.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([N:20]2[CH2:31][CH2:30][C:23]([NH2:27])([C:24]([OH:34])=[O:29])[CH2:22][CH2:21]2)=[O:19])=[C:12]([Cl:32])[C:11]=1[Cl:33]

Participants

8

Reactant 4

HCID 8471Triethylamine2×HCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 20765643HCID 20765643, compound

Product 1

HCID 20765639HCID 20765639, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent3×

Procedure

To a suspension of Example 355 (700 mg, 1.4 mmol) in DME (10 mL) was added a solution of (BOC)2O (1.51 g, 6.9 mmol) in DME (5 mL), triethylamine (0.23 mL, 1.7 mmol) and DMAP (9 mg, 0.07 mmol). The reaction mixture was stirred at room temperature overnight. Additional triethylamine (0.23 mL) and DMAP (30 mg) were added, and the mixture was heated at 60° C. for 6 hours. After aqueous work up, the crude product was suspended in DME (5 mL) and water (5 mL) containing 200 mg of NaOH. The suspension was stirred for 5 hours at room temperature, and separated by HPLC to give the title compound (300 mg, 45%). 1H NMR (300 MHz, DMSO-d6) δ 1.78 (m, 2H), 2.10 (m, 2H), 3.60 (m, 2H), 3.80 (s, 3H), 3.86 (m, 2H), 6.58 (d, 1H), 7.10 (d, 1H), 7.25 (d, 1H), 7.28 (d, 1H), 7.50 (d, 1H), 7.58 (t, 1H), 7.77 (d, 1H), 7.80 (d, 1H), 8.50 (br s, 2H). MS (ESI+) m/z 481 (M+H)+. Anal calcd for C22H22N2Cl2SO4.0.75H2O: C, 47.34; H, 4.06; N, 4.60. Found: C, 47.31; H, 4.05; N, 4.43.

Workup

  1. temperaturethe mixture was heated at 60° C. for 6 hours
  2. stirringThe suspension was stirred for 5 hours at room temperature
  3. customseparated by HPLC

Sources & evidence

ORD record
ord-403dc7d0ffbc4740ad9a45d5f337e35d
Source dataset
uspto-grants-2005_03
Patent number
US06867203B2

Reaction notes

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