Potassium Bromide → HCID 76497815, compound

HRID 975947Notes

Reaction equation

HRID 975947 reaction equation
[NH2:1][CH2:2][C:3]([N:5]1[CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][CH2:14][CH:6]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[O:4].[K+].[Br-].[N:25]([C:28]1[CH:29]=[C:30]([CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH:31]=[CH:32][CH:33]=1)=[C:26]=[O:27]>O1CCCC1>[C:10]([O:9][C:7]([CH:6]1[CH2:14][CH2:15][CH:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:5]1[C:3](=[O:4])[CH2:2][NH:1][C:26](=[O:27])[NH:25][C:28]1[CH:29]=[C:30]([CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH:31]=[CH:32][CH:33]=1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 253877Potassium BromideHCID 18928063HCID 18928063, compoundHCID 19070835Methyl 3-isocyanatophenylacetate

Product 1

HCID 76497815HCID 76497815, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

By proceeding in a fashion similar to that described in Example 2, but starting from 6.2 g of tert-butyl (2RS,5SR)-1-(2-aminoacetyl)-5-phenylprolinate in solution in 150 cm3 of anhydrous tetrahydrofuran and 4.2 g of methyl 3-isocyanatophenylacetate, 6 g of methyl (2RS,5SR)-3-{3-[2-(2-tert-butoxycarbonyl-5-phenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}phenylacetate are obtained [proton NMR (200 MHz, DMSO D6, δ in ppm), 2 rotamers at room temperature, peak coalescence at 120° C.: 1.5 (s, 9H, (CH3)3); 3.6 (s, 2H, CH2CO); 3.65 (s, 3H, OCH3); 6.8 to 7.7 (m, 9H, aromatic). Infrared spectrum (KBr), characteristic bands in cm-1 : 3365, 3155, 3110, 3090, 3060, 3030, 2975, 2950, 2930, 2875, 1738, 1700, 1650, 1610, 1595, 1560, 1495, 1435, 1395, 1365, 1315, 1250, 1220, 1155, 1015, 905, 890, 860, 845, 780, 760, 700].

Sources & evidence

ORD record
ord-856d8b6f9d724a709b518ac660e4fa9b
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

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