Methylamine → HCID 131723110, compound

HRID 1698932Notes

Reaction equation

HRID 1698932 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C@H:24]([NH:29][C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=1.CN>C1COCC1>[NH2:3][O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:23][C@H:24]([NH:29][C:30]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[O:31])[C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 70167850HCID 70167850, compound

Product 1

HCID 131723110HCID 131723110, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 78 mg (0.15 mmol) of methyl (2S)-3-{4-[3-(1,3-dioxoisoindolin-2-yloxy)propoxy]phenyl}-2-[(phenylmethoxy)carbonylamino]propanoate, as prepared in the preceding step, in 5 mL THF was added 0.4 mL of 2M methylamine solution in THF. The solution was stirred at room temperature for 3 h. The solvent was then removed under reduced pressure. The mixture was chromatographed on a silica gel column using EtOAc/hexanes (3:7 to 7:3 v/v) as eluent to yield 47 mg (80%) of viscous liquid as product: 1H NMR (300 MHz, CDCl3) δ7.38-7.28 (m, 5H), 6.98 (d, J=8.70 Hz, 2H), 6.79 (d, J=8.70 Hz, 2H), 5.20 (d, J=8.20 Hz, 1H), 5.10 (d, J=12.34 Hz, 1H), 5.05 (d, J=12.34 Hz, 1H), 4.60 (m, 1H), 3.99 (t, J=6.30 Hz, 2H), 3.84 (t, J=6.20 Hz, 2H), 3.71 (s, 3H), 3.10-2.97 (m, 2H), 2.05 (quintet, J=6.24 Hz, 2H).

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customThe mixture was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-1fc2836346344735b8bf30dce147f99c
Source dataset
uspto-grants-2002_02
Patent number
US06344484B1

Reaction notes

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