Hydrochloric Acid → HCID 67563471, compound

HRID 612387Notes

Reaction equation

HRID 612387 reaction equation
C[O:2][C:3](=[O:36])[C@H:4]([CH2:16][NH:17][C:18](=[O:35])[CH2:19][C@H:20]1[O:24][N:23]([CH3:25])[C@@H:22]([C:26]2[CH:31]=[CH:30][C:29]([CH:32]=[N:33][NH2:34])=[CH:28][CH:27]=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:37]>>[ClH:37].[CH3:25][N:23]1[C@@H:22]([C:26]2[CH:27]=[CH:28][C:29]([CH:32]=[N:33][NH2:34])=[CH:30][CH:31]=2)[CH2:21][C@@H:20]([CH2:19][C:18]([NH:17][CH2:16][C@@H:4]([C:3]([OH:36])=[O:2])[NH:5][S:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[CH:10]=2)(=[O:8])=[O:7])=[O:35])[O:24]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86754962HCID 86754962, compound

Product 1

HCID 67563471HCID 67563471, compoundYield 90%

Procedure

Cis-3-[2-[2-methyl-3-[4-(aminoiminomethyl)phenyl]-isoxazolidin-5-yl] -acetyl] amino-N-(3-methylphenylsulfonyl)-L-alanine methyl ester(100 mg, 0.19 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. 1H NMR(300 MHz, DMSO-d6)δ2.24(m, 1H), 2.38(s, 3H), 2.54(s, 3H), 2.60(m, 1H), 2.98(m, 1H), 3.08(m, 1H), 3.22(m,1H), 3.36(m, 1H), 3.86(m, 1H), 4.40(m,1H), 4.74(m, 1H), 7.43(m, 2H), 7.38(m, 2H), 7.80(d, J=7, 1H), 7.94(d, J=7, 2H), 8.20(m, 2H); MS(ESI) Calc. for (M+1)+ : 504. Found: 504.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-f91a00c84356425c842555b11a182c67
Source dataset
uspto-grants-1999_12
Patent number
US06004955

Reaction notes

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