Toluene → HCID 68488356, compound

HRID 1822460Notes

Reaction equation

HRID 1822460 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:21]=3)[CH2:16][NH:15]2)=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].[C:38]([O-:41])(O)=O.[Na+].C(Cl)(Cl)=O.C1(C)C=CC=CC=1.[CH3:54][O:55][C:56]1[CH:65]=[CH:64][CH:63]=[CH:62][C:57]=1[O:58][CH2:59][CH2:60][NH2:61]>C1COCC1>[CH2:1]([O:3][C:4]([C@@:6]1([NH:11][C:12]([C@@H:14]2[CH2:18][C@@H:17]([O:19][C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:21]=3)[CH2:16][N:15]2[C:38](=[O:41])[NH:61][CH2:60][CH2:59][O:58][C:57]2[CH:62]=[CH:63][CH:64]=[CH:65][C:56]=2[O:55][CH3:54])=[O:13])[CH2:8][C@H:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]

Participants

7

Reactant 5

HCID 1140TolueneHCID 6371PhosgeneHCID 516892Sodium Bicarbonate2×HCID 17130052-(2-Methoxyphenoxy)ethyl amineHCID 207653161-{[4-(7-Methoxy-2-phenyl-quinolin-4-yloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 68488356HCID 68488356, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 12 (0.06 mmol) in THF (2 mL), was added a large excess of NaHCO3 (s) and a solution of phosgene in toluene (0.078 mmol). After 10 min of agitation the slurry was filtered and concentrated to dryness. The solid was redissolved in dichloromethane and a large excess of NaHCO3 (s) and 2-(2-methoxy-phenoxy)-ethylamine (15 mg, 0.09 mmol) was added. The slurry was agitated for 30 hrs at RT. The slurry was filtered, concentrated to dryness, redissolved in MeOH and subjected HPLC purification to give the title compound (10.6 mg, 0.015 mmol). Purity by HPLC >95%. M+H+695.17.

Workup

  1. filtrationAfter 10 min of agitation the slurry was filtered
  2. concentrationconcentrated to dryness
  3. dissolutionThe solid was redissolved in dichloromethane
  4. filtrationThe slurry was filtered
  5. concentrationconcentrated to dryness
  6. dissolutionredissolved in MeOH
  7. customHPLC purification

Sources & evidence

ORD record
ord-7d65f8e888fb4866a765cf62061a6a60
Source dataset
uspto-grants-2009_10
Patent number
US07608590B2

Reaction notes

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