Methoxyacetic Acid → HCID 131724234, compound

HRID 432113Notes

Reaction equation

HRID 432113 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[O:17][C@H:16]([CH2:21][N:22]([CH2:30][C@H:31]([O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])[C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:15][CH2:14]3)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].[CH3:46][O:47][CH2:48][C:49](O)=[O:50].CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Si:39]([O:38][C@H:31]([C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1)[CH2:30][N:22]([CH2:21][C@@H:16]1[CH2:15][CH2:14][C:13]2[C:18](=[CH:19][CH:20]=[C:11]([C:7]3[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([NH:1][C:49](=[O:50])[CH2:48][O:47][CH3:46])(=[O:4])=[O:3])[CH:6]=3)[CH:12]=2)[O:17]1)[C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:27])[CH3:28])([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:40])[CH3:41]

Participants

6

Reactant 3

HCID 12251Methoxyacetic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 91477717HCID 91477717, compound

Product 1

HCID 131724234HCID 131724234, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of the compound of Example 281 (60 mg, 0.091 mmol), methoxyacetic acid (13 mg, 0.13 mmol), EDCI (26 mg, 0.14 mmol), and DMAP (11 mg, 0.091 mmol) in CH2Cl2 (1.5 mL) was stirred at room temperature overnight. The reaction mixture was concentrated down and the crude product was purified by preparative TLC plate with CH2Cl2:MeOH:NH4OH (90:15:2) to obtain (60 mg). ESLC-MS: m/z=725 (MH+); 1H NMR (MeOH-d4): 8.566˜8.439 (m, 2H), 8.077 (s, 1H), 7.889˜7.780 (m, 1H), 7.675 (m, 1H), 7.453 (m, 2H), 7.313 (m, 2H), 6.767 (d, 1H), 5.180˜5.035 (m, 1H), 4.220 (s, b, 1H), 3.907 (s, 2H), 3.760˜3.333 (m, 4H), 2.835 (m, 2H), 2.041 (m, 1H), 1.711 (m, 1H), 1.445 (d, 9H), 0.892 (s, 9H), 0.076 (s, 3H), −0.109 (s, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated down
  2. customthe crude product was purified by preparative TLC plate with CH2Cl2:MeOH:NH4OH (90:15:2)
  3. customto obtain (60 mg)

Sources & evidence

ORD record
ord-22afc2d00a8844ad90402c3321c37ace
Source dataset
uspto-grants-2003_12
Patent number
US06660752B2

Reaction notes

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