Methyl chloroformate → HCID 18512233, compound

HRID 1370863Notes

Reaction equation

HRID 1370863 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:36]=[CH:37][CH:38]=1)[O:8][C:9]1[CH:35]=[CH:34][C:12]([CH2:13][N:14]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:15]2[C:16]([CH3:26])=[C:17]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH:18]=[CH:19][CH:20]=2)=[CH:11][CH:10]=1.Cl[C:40]([O:42][CH3:43])=[O:41]>C1COCC1>[CH2:27]([N:14]([CH2:13][C:12]1[CH:11]=[CH:10][C:9]([O:8][C:7]2[CH:6]=[C:5]([CH:38]=[CH:37][CH:36]=2)[O:4][CH2:3][CH2:2][NH:1][C:40](=[O:41])[O:42][CH3:43])=[CH:35][CH:34]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[C:16]=1[CH3:26])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 18512193HCID 18512193, compound

Product 1

HCID 18512233HCID 18512233, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 78C (0.050 g, 0.0942 mmoles) in anhydrous THF (1 mL) was treated with methyl chloroformate (0.009 mL, 0.113 mmoles) and mixed overnight at room temperature. Reaction mixture concentrated under reduced pressure, and the residue was purified by preparative HPLC (CH3CN:0.1% trifluoroacetic acid in H2O) on a YMC ODS Guardpak column to provide the title compound. 1H NMR (300 MHz, CDCl3) δ7.10-7.30 (mn, 10 H), 6.95 (m, 1 H), 6.89 (d, 2 H), 6.55 (m, 2 H), 6.43 (s, 1 H), 6.26 (d, 1 H), 5.15 (br.s, 1 H), 4.00-4.20 (m, 4 H), 3.96 (t, 2 H), 3.68 (s, 3 H), 3.55 (m, 2 H), 2.90 (s, 3 H), 2.30 (s, 3 H); MS (ESI+) m/z 590 (M+H)+.

Workup

  1. additionmixed overnight at room temperature
  2. customReaction mixture
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was purified by preparative HPLC (CH3CN:0.1% trifluoroacetic acid in H2O) on a YMC ODS Guardpak column

Sources & evidence

ORD record
ord-310874fd3d07492e9f7dace8fcc8911c
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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