Chlorotrimethylsilane → (S)-1-(10,11-dihydro-5H-dibenz [b,f]azepine-5-carbonyl)-4-(benzyloxycarbonyl)piperazine-2-carboxylic acid

HRID 486756Notes

Reaction equation

HRID 486756 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][NH:14][C@H:13]([C:17]([OH:19])=[O:18])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[Si](C)(C)C.C(N(CC)C(C)C)(C)C.[CH:34]1[C:44]2[CH2:43][CH2:42][C:41]3[CH:45]=[CH:46][CH:47]=[CH:48][C:40]=3[N:39]([C:49](Cl)=[O:50])[C:38]=2[CH:37]=[CH:36][CH:35]=1>>[CH:34]1[C:44]2[CH2:43][CH2:42][C:41]3[CH:45]=[CH:46][CH:47]=[CH:48][C:40]=3[N:39]([C:49]([N:14]3[CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:10])[CH2:12][C@H:13]3[C:17]([OH:19])=[O:18])=[O:50])[C:38]=2[CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 81531DiisopropylethylamineHCID 11857910,11-Dihydro-5H-dibenz[b,f]azepine-5-carbonyl chlorideHCID 1514273(S)-4-(Benzyloxycarbonyl)piperazine-2-carboxylic acid

Product 1

HCID 54116854(S)-1-(10,11-dihydro-5H-dibenz [b,f]azepine-5-carbonyl)-4-(benzyloxycarbonyl)piperazine-2-carboxylic acidYield 24%

Procedure

Following the procedure of Example 16, Step B, 811 mg (2.5 mmole) of (S)-4-(benzyloxycarbonyl)-piperazine-2-carboxylic acid (from Example 7, Step A) 680 mg (6.26 mmole) of chlorotrimethylsilane, 1.23 g (9.5 mmole) of N,N-diisopropylethylamine and 665 mg (2.5 mmole ) of 97% of 10,11-dihydro-5H-dibenz[b,f]-azepine -5-carbonyl chloride, gave 284 mg (24%) of (S)-1-(10,11-dihydro-5H-dibenz[b,f]azepine5-carbonyl)-4-(benzyloxycarbonyl)piperazine-2-carboxylic acid, mp 185° C. (softened >90° C.); TLC Rf 0.68 (Analtech SGF plates developed with isoamyl alcohol:acetone:water [5:2:1]).

Sources & evidence

ORD record
ord-14417fcbd3f3489ea0d62f69a931a28d
Source dataset
uspto-grants-1994_03
Patent number
US05292726

Reaction notes

Loading…