Hydrochloric Acid → HCID 67563487, compound

HRID 612388Notes

Reaction equation

C[O:2][C:3](=[O:38])[C@H:4]([CH2:16][NH:17][C:18](=[O:37])[CH2:19][C@H:20]1[O:25][C:24](=[O:26])[N:23]([CH3:27])[C@@H:22]([C:28]2[CH:33]=[CH:32][C:31]([CH:34]=[N:35][NH2:36])=[CH:30][CH:29]=2)[CH2:21]1)[NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=1)(=[O:8])=[O:7].[ClH:39]>>[ClH:39].[NH2:36][N:35]=[CH:34][C:31]1[CH:30]=[CH:29][C:28]([C@H:22]2[CH2:21][C@@H:20]([CH2:19][C:18]([NH:17][CH2:16][C@@H:4]([C:3]([OH:38])=[O:2])[NH:5][S:6]([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=3)(=[O:8])=[O:7])=[O:37])[O:25][C:24](=[O:26])[N:23]2[CH3:27])=[CH:33][CH:32]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 67562575HCID 67562575, compound

Product 1

HCID 67563487HCID 67563487, compoundYield 90%

Procedure

Cis-3-[[[4-[4-(aminoiminomethyl)phenyl]tetrahydro-3-methyl-2-oxo-2H-1,3-oxazin-6-yl]acetyl]amino]-N-[(3-methylphenyl)sulfonyl]-L-alanine methyl ester(30 mg, 0.06 mmol) was dissolved in 3N HCl(3 ml). The resulting solution was stirred at rt for 36 hrs and then concentrated to yield the acid as an amorphous solid(90 mg, 90% yield). The acid was further purified by reverse HPLC using water and 0.1% TFA in acetonitrile as eluent. MS(ESI) Calc. for (M+1)+ : 532. Found: 532.

Workup

concentrationconcentrated

Sources & evidence

ORD record: ord-4d5c6776489a4cdda523bbba5aaa30eb
Source dataset: uspto-grants-1999_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06004955

Reaction notes

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