Hydrochloric Acid → benzyl (1S,3S,4S)-4-amino-3-hydroxy-5-phenyl-1-[4-(2-pyridinyl)benzyl]pentylcarbamate

HRID 1174336Notes

Reaction equation

C(OC([NH:8][C@@H:9]([CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C@@H:10]([OH:37])[CH2:11][C@@H:12]([NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:16][CH:15]=1)=O)(C)(C)C.Cl>C1COCC1>[NH2:8][C@@H:9]([CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C@@H:10]([OH:37])[CH2:11][C@@H:12]([NH:26][C:27](=[O:36])[O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution containing the product from Example 1C (0.088 g, 0.15 mmol) in a mixture of THF (2 mL) and aqueous HCl (0.26 mL, 4 N) was stirred at 25° C. for 16 hours, then heated at 60° C. for 2 hours, cooled and concentrated. The residue was treated with ethanol and concentrated several times to give the title compound as the hydrochloride salt, which was used without further purification.

Workup

temperatureheated at 60° C. for 2 hours
temperaturecooled
concentrationconcentrated
additionThe residue was treated with ethanol
concentrationconcentrated several times

Sources & evidence

ORD record: ord-724200c5df354c3887e0bb96e208c419
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834043B2

Reaction notes

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