Water → HCID 68454720, compound

HRID 2085801Notes

Reaction equation

HRID 2085801 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C@@H:6]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:25][C:26](=[O:43])[C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:42][CH2:41][C:36]4([CH2:40][CH2:39][CH2:38][CH2:37]4)[CH2:35][CH2:34]3)=[CH:29][CH:28]=2)(=[O:24])=[O:23])=[CH:18][C:17]=1[N+:44]([O-:46])=[O:45])[CH2:7][S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[O-:47][C:48]#[N:49].[K+].O>CO>[NH2:49][C:48]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][C@@H:6]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH:25][C:26](=[O:43])[C:27]2[CH:28]=[CH:29][C:30]([N:33]3[CH2:34][CH2:35][C:36]4([CH2:37][CH2:38][CH2:39][CH2:40]4)[CH2:41][CH2:42]3)=[CH:31][CH:32]=2)(=[O:24])=[O:23])=[CH:18][C:17]=1[N+:44]([O-:46])=[O:45])[CH2:7][S:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:47]

Participants

5

Reactant 3

HCID 962WaterHCID 11378442Potassium cyanateHCID 69058342HCID 69058342, compound

Product 1

HCID 68454720HCID 68454720, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Example 287 (60 mg, 0.1 mmol) and potassium cyanate (20 mg, 0.25 mmol) in methanol (1 mL) was stirred at 55° C. for 1.5 hours, cooled to room temperature, treated with water, and extracted with dichloromethane. The combined extracts were washed with saturated sodium bicarbonate, dried (MgSO4), filtered, and concentrated. The concentrate was purified by reverse phase HPLC with 0-100% acetonitrile/water containing 0.1% TFA to provide the desired product. MS (ESI(+)) m/e 709 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ11.97 (s, 1H), 8.53 (d, 1H), 8.32 (d, 1H), 7.85 (dd, 1H), 7.73 (d, 2H), 7.25-7.10 (m, 6H), 6.93 (d, 2H), 5.90 (s, 1H), 4.10 (m, 1H), 3.34 (m, 6H), 2.91 (t, 2H), 1.75 (m, 2H), 1.59 (m, 4H), 1.42 (m, 8H), 1.34 (m, 4H).

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined extracts were washed with saturated sodium bicarbonate
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was purified by reverse phase HPLC with 0-100% acetonitrile/water containing 0.1% TFA

Sources & evidence

ORD record
ord-5b9a6aa8d8374061b2ab5ec9a17caaff
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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