Pyridine → HCID 53913232, compound

HRID 375767Notes

Reaction equation

C([Si](C)(C)[O:6][C:7]1[C:22]2[CH2:21][S:20][CH2:19][C@@H:18]([C:23]([O:25][CH3:26])=[O:24])[NH:17][C:16](=[O:27])[C@@H:15]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:14][O:13][C:12](=[O:36])[C:11]=2[CH:10]=[C:9]([N:37]2C(=O)C3[C:39](=CC=CC=3)[C:38]2=[O:47])[CH:8]=1)(C)(C)C.N1C=CC=CC=1>C(OC(=O)C)(=O)C>[C:38]([NH:37][C:9]1[CH:8]=[C:7]([OH:6])[C:22]2[CH2:21][S:20][CH2:19][C@@H:18]([C:23]([O:25][CH3:26])=[O:24])[NH:17][C:16](=[O:27])[C@@H:15]([NH:28][C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])[CH2:14][O:13][C:12](=[O:36])[C:11]=2[CH:10]=1)(=[O:47])[CH3:39]

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of 25 mg of the product of Example 159 and 0.1 ml of pyridine in 1.5 ml of acetic anhydride was stirred at 20° C. for 3 hours. The precipitate was collected by filtration, washed with pentane, and dissolved in 1.5 ml of methanol. After the addition of 2.6 mg of potassium carbonate, the mixture was stirred for 1.5 hours at 20° C., and then evaporated in vacuo. Water was added to the residue, and the insoluble material was isolated by filtration, to yield 7 mg of tert-butyl (4R,7S)-12-acetylamino-1,3,4,5,6,7,8,10-octahydro-14-hydroxy-4-methoxycarbonyl-6,10-dioxo-9,2,5-benzoxathiaazacyclododecine-7-carbamate as a white solid.

Workup

filtrationThe precipitate was collected by filtration
washwashed with pentane
dissolutiondissolved in 1.5 ml of methanol
additionAfter the addition of 2.6 mg of potassium carbonate
stirringthe mixture was stirred for 1.5 hours at 20° C.
customevaporated in vacuo
additionWater was added to the residue
customthe insoluble material was isolated by filtration

Sources & evidence

ORD record: ord-3f80976e62ba4e6bb1a65c5ab68b348a
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05486466

Reaction notes

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