Hydrochloric Acid → HCID 10054458, compound

HRID 1684761Notes

Reaction equation

HRID 1684761 reaction equation
C([O:5][C:6](=[O:54])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:46])[NH:16][CH2:17][C@H:18]([CH:43]([CH3:45])[CH3:44])[CH2:19][C@H:20]([NH:35]C(OC(C)(C)C)=O)[C@@H:21]([OH:34])[CH2:22][C@H:23]([C:27](=[O:33])[NH:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:24]([CH3:26])[CH3:25])=[C:11]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][O:52][CH3:53])[CH:10]=1)(C)(C)C.Cl>O1CCOCC1>[NH2:35][C@H:20]([C@@H:21]([OH:34])[CH2:22][C@H:23]([C:27](=[O:33])[NH:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH:24]([CH3:26])[CH3:25])[CH2:19][C@@H:18]([CH:43]([CH3:44])[CH3:45])[CH2:17][NH:16][C:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:6]([OH:54])=[O:5])=[CH:10][C:11]=1[O:47][CH2:48][CH2:49][CH2:50][CH2:51][O:52][CH3:53])=[O:46]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57032209HCID 57032209, compound

Product 1

HCID 10054458HCID 10054458, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

After reaction of (2S,4S,5S,7S)-{4-[4-(tert-butoxycarbonyl)amino-7-butylcarbamoyl-5-hydroxy-2-isopropyl-8-methyl-nonylcarbamoyl]-3-(4-methoxybutoxy)-phenoxy}-acetic acid (tert-butyl) ester (93 mg) in a 4N hydrochloric acid solution in dioxane (2 ml) at 0° C. for 45 minutes and then at room temperature for 13 hours, the solvent is rapidly concentrated under a high vacuum with vigorous stirring until frozen and is subsequently removed by lyophilisation. (2S,4S,5S,7S)-[4-(4-Amino-7-butylcarbamoyl-5-hydroxy-2-isopropyl-8-methyl-nonylcarbamoyl)-3-(4-methoxybutoxy)-phenoxy]-acetic acid is obtained: HPLC Rt =11.7 min. MS(FAB) m/e 610 (M+ +1).

Workup

  1. concentrationthe solvent is rapidly concentrated under a high vacuum
  2. temperatureuntil frozen
  3. customis subsequently removed by lyophilisation

Sources & evidence

ORD record
ord-90b31899bb084f59815af0fcc26c8d10
Source dataset
uspto-grants-1997_06
Patent number
US05641778

Reaction notes

Loading…