Hydrochloric Acid → (S)-3-[(S)-2-(4-acetoxy-phenyl)-2,3-dihydro-benzo[1,4]dioxin-6-yl]-2-(4-nitro-benzenesulfonylamino)-propionic acid methyl ester

HRID 391795Notes

Reaction equation

HRID 391795 reaction equation
COC(=O)[C@@H](NC(OC(C)(C)C)=O)CC1C=CC2O[C@@H](C3C=CC(OC(=O)C)=CC=3)COC=2C=1.Cl.[CH3:36][O:37][C:38](=[O:62])[C@@H:39]([NH2:61])[CH2:40][C:41]1[CH:60]=[CH:59][C:44]2[O:45][C@@H:46]([C:49]3[CH:54]=[CH:53][C:52]([O:55][C:56](=[O:58])[CH3:57])=[CH:51][CH:50]=3)[CH2:47][O:48][C:43]=2[CH:42]=1.[N+:63]([C:66]1[CH:71]=[CH:70][C:69]([S:72](Cl)(=[O:74])=[O:73])=[CH:68][CH:67]=1)([O-:65])=[O:64]>>[CH3:36][O:37][C:38](=[O:62])[C@@H:39]([NH:61][S:72]([C:69]1[CH:68]=[CH:67][C:66]([N+:63]([O-:65])=[O:64])=[CH:71][CH:70]=1)(=[O:73])=[O:74])[CH2:40][C:41]1[CH:60]=[CH:59][C:44]2[O:45][C@@H:46]([C:49]3[CH:50]=[CH:51][C:52]([O:55][C:56](=[O:58])[CH3:57])=[CH:53][CH:54]=3)[CH2:47][O:48][C:43]=2[CH:42]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 74044-Nitrobenzenesulfonyl chlorideHCID 58327221(S)-3-[(S)-2-(4-Acetoxy-phenyl)-2,3-dihydro-benzo[1,4]dioxin-6-yl]-2-tert-butoxycarbonylamino-propionic acid methyl esterHCID 67251459(S)-3-[(S)-2-(4-acetoxy-phenyl)-2,3-dihydro-benzo[1,4]dioxin-6-yl]-2-amino-propionic acid methyl ester

Product 1

HCID 58327066(S)-3-[(S)-2-(4-acetoxy-phenyl)-2,3-dihydro-benzo[1,4]dioxin-6-yl]-2-(4-nitro-benzenesulfonylamino)-propionic acid methyl ester

Procedure

(S)-3-[(S)-2-(4-Acetoxy-phenyl)-2,3-dihydro-benzo[1,4]dioxin-6-yl]-2-tert-butoxycarbonylamino-propionic acid methyl ester (208 mg) was converted to the HCl salt of (S)-3-[(S)-2-(4-acetoxy-phenyl)-2,3-dihydro-benzo[1,4]dioxin-6-yl]-2-amino-propionic acid methyl ester according to General Procedure C. This intermediate was further reacted with 4-nitrobenzenesulfonyl chloride as described in General Procedure F to furnish (S)-3-[(S)-2-(4-acetoxy-phenyl)-2,3-dihydro-benzo[1,4]dioxin-6-yl]-2-(4-nitro-benzenesulfonylamino)-propionic acid methyl ester (230 mg). LCMS (m/z): 558.

Sources & evidence

ORD record
ord-5076513c442d40159d51532e25799007
Source dataset
uspto-grants-2013_02
Patent number
US08383644B2

Reaction notes

Loading…