Hydrochloric Acid → (4-((1E,4E)-2-amino-4-((3R,4R)-3,4-dihydroxypyrrolidine-1-carbonyl)-3H-benzo[b]azepin-8-yl)phenyl)(pyrrolidin-1-yl)methanone

HRID 37997Notes

Reaction equation

HRID 37997 reaction equation
Cl.C(OC([NH:9][C:10]1[CH2:11][C:12]([C:34](O)=[O:35])=[CH:13][C:14]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([N:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)=[O:28])=[CH:23][CH:22]=3)=[CH:17][C:15]=2[N:16]=1)=O)(C)(C)C.[Si]([O:44][C@H:45]1[C@H:49]([O:50][Si](C(C)(C)C)(C)C)[CH2:48][NH:47][CH2:46]1)(C(C)(C)C)(C)C>>[NH2:9][C:10]1[CH2:11][C:12]([C:34]([N:47]2[CH2:48][C@@H:49]([OH:50])[C@H:45]([OH:44])[CH2:46]2)=[O:35])=[CH:13][C:14]2[CH:20]=[CH:19][C:18]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([N:29]4[CH2:30][CH2:31][CH2:32][CH2:33]4)=[O:28])=[CH:25][CH:26]=3)=[CH:17][C:15]=2[N:16]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 24727995(3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)pyrrolidineHCID 66960164(1E,4E)-2-(tert-butoxycarbonylamino)-8-(4-(pyrrolidine-1-carbonyl)phenyl)-3H-benzo[b]azepine-4-carboxylic acid

Product 1

HCID 58267264(4-((1E,4E)-2-amino-4-((3R,4R)-3,4-dihydroxypyrrolidine-1-carbonyl)-3H-benzo[b]azepin-8-yl)phenyl)(pyrrolidin-1-yl)methanone

Procedure

The title compound was prepared by the procedures as described in Example 101 (Steps H and I) with conc. HCl instead of TFA using (1E,4E)-2-(tert-butoxycarbonylamino)-8-(4-(pyrrolidine-1-carbonyl)phenyl)-3H-benzo[b]azepine-4-carboxylic acid and (3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)pyrrolidin.

Sources & evidence

ORD record
ord-e697edadcf7f4e1a9a543a6568385c47
Source dataset
uspto-grants-2013_09
Patent number
US08524702B2

Reaction notes

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