Diisopropylethylamine → HCID 11611023, compound

HRID 2242203Notes

Reaction equation

HRID 2242203 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([CH2:13][NH2:14])[CH2:10][C@H:9]1[C:15]([N:17]1[CH2:21][CH2:20][S:19][CH2:18]1)=[O:16])=O)(C)(C)C.C(N(CC)C(C)C)(C)C.Cl[S:32]([C:35]1[CH:43]=[CH:42][C:38]([C:39]([OH:41])=[O:40])=[CH:37][CH:36]=1)(=[O:34])=[O:33]>C1COCC1>[S:19]1[CH2:20][CH2:21][N:17]([C:15]([C@H:9]2[NH:8][CH2:12][C@@H:11]([CH2:13][NH:14][S:32]([C:35]3[CH:36]=[CH:37][C:38]([C:39]([OH:41])=[O:40])=[CH:42][CH:43]=3)(=[O:34])=[O:33])[CH2:10]2)=[O:16])[CH2:18]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 823854-(Chlorosulfonyl)benzoic acidHCID 69241294HCID 69241294, compound

Product 1

HCID 11611023HCID 11611023, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 17D (32 mg, 0.1 mmol) in anhydrous THF (5 mL) was added N,N-diisopropylethylamine (0.035 mL, 0.2 mmol) followed by 4-chlorosulfonyl-benzoic acid (20.92 mg, 0.12 mmol). The mixture was stirred for 8 hours at room temperature and concentrated under reduced pressure. The residue was taken up in anhydrous dichloromethane (3 mL) and trifluoroacetic acid (0.075 mL) in dichloromethane (0.075 mL) was added and the mixture was allowed to stir for 5 hours at room temperature. The mixture was concentrated under reduced pressure and purified using RP-HPLC to provide the titled compound. MS (ESI) m/e 400 (M+H)+, 398 (M−H)−; 1H NMR (500 MHz, CD3OD) δ ppm 1.78 (m, 1 H) 2.65 (m, 1 H) 3.00 (m, 2 H) 3.08 (m, 1 H) 3.14 (m, 1 H) 3.20 (m, 1 H) 3.49 (m, 1 H) 3.60 (m, 1 H) 3.73 (m, 1H) 3.88 (m, 1 H) 4.50 (m, 1 H) 4.66 (m, 2 H) 7.95 (d, 2 H) 8.19 (d, 2 H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiontrifluoroacetic acid (0.075 mL) in dichloromethane (0.075 mL) was added
  3. stirringto stir for 5 hours at room temperature
  4. concentrationThe mixture was concentrated under reduced pressure
  5. custompurified

Sources & evidence

ORD record
ord-17e8735ea96f47798d3c2157daaad816
Source dataset
uspto-grants-2010_03
Patent number
US07671076B2

Reaction notes

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