Triethylamine → N-[2-[[5-{2,8-Dimethyl-5H-dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2-oxo4-thioxo-1(2H)-pyrimidinyl]methyl]thiazol-4-ylcarbonyl]-L-aspartic acid, dimethyl ester

HRID 1275888Notes

Reaction equation

HRID 1275888 reaction equation
[CH3:1][C:2]1[CH:34]=[CH:33][C:5]2[CH:6]([C:16]3[C:17](=[S:32])[NH:18][C:19](=[O:31])[N:20]([CH2:22][C:23]4[S:24][CH:25]=[C:26]([C:28]([OH:30])=O)[N:27]=4)[CH:21]=3)[C:7]3[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:8]=3[CH:9]=[CH:10][C:4]=2[CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:47][O:48][C:49](=[O:57])[C@H:50]([CH2:52][C:53]([O:55][CH3:56])=[O:54])[NH2:51].C(N(CC)CC)C>CN(C)C=O>[CH3:15][C:12]1[CH:13]=[CH:14][C:7]2[CH:6]([C:16]3[C:17](=[S:32])[NH:18][C:19](=[O:31])[N:20]([CH2:22][C:23]4[S:24][CH:25]=[C:26]([C:28]([NH:51][C@H:50]([C:49]([O:48][CH3:47])=[O:57])[CH2:52][C:53]([O:55][CH3:56])=[O:54])=[O:30])[N:27]=4)[CH:21]=3)[C:5]3[CH:33]=[CH:34][C:2]([CH3:1])=[CH:3][C:4]=3[CH:10]=[CH:9][C:8]=2[CH:11]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 1112071,4-Dimethyl L-aspartateHCID 221172312-[[5-{2,8-Dimethyl-5H-dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2-oxo-4-thioxo-1(2H)-pyrimidinyl]methyl]-4-thiazolecarboxylic acid

Product 1

HCID 131722226N-[2-[[5-{2,8-Dimethyl-5H-dibenzo[a,d]cyclohepten-5-yl}-3,4-dihydro-2-oxo4-thioxo-1(2H)-pyrimidinyl]methyl]thiazol-4-ylcarbonyl]-L-aspartic acid, dimethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from example 8(0.4 g) was dissolved in dry dimethylformamide (15 ml) and treated with N,N-carbonyldiimidazole (0.16 g). After 30 minutes L-aspartic acid dimethyl ester (0.32 g) was added followed by triethylamine (0.5 ml). The mixture was stirred overnight and partitioned between ethyl acetate and 2M HCl. The organic phase was washed with brine, dried (MgSO4), evaporated and purified by chromatography eluting with 50% ethyl acetate in dichloromethane. Used directly in the next step.

Workup

  1. custompartitioned between ethyl acetate and 2M HCl
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. custompurified by chromatography
  6. washeluting with 50% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-12675a682fa14479ba65271d789b59f9
Source dataset
uspto-grants-2000_12
Patent number
US06162808

Reaction notes

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