Methyl 2-iodopropanoate → 6-t-Butoxycarbonylamino-4-N-(1-carbomethoxyethyl)-perhydro-1,4-thiazepin-5-one

HRID 1981893Notes

Reaction equation

HRID 1981893 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:15][S:14][CH2:13][CH2:12][NH:11][C:10]1=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].I[CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20]>>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:15][S:14][CH2:13][CH2:12][N:11]([CH:18]([C:19]([O:21][CH3:22])=[O:20])[CH3:23])[C:10]1=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 143426Methyl 2-iodopropanoateHCID 15591256(Hexahydro-5-oxo-1,4-thiazepin-6-yl)carbamic acid, (1,1-dimethylethyl) ester

Product 1

HCID 233180436-t-Butoxycarbonylamino-4-N-(1-carbomethoxyethyl)-perhydro-1,4-thiazepin-5-oneYield 81.5%

Procedure

The above-named compound is prepared from 6-t-butoxycarbonylamino-perhydro-1,4-thiazepin-5-one (0.1 g) and methyl iodopropionate (0.11 g) according to the procedure described in Example 4. The product (0.11 g) is obtained after chromatography. The NMR spectrum is consistent with the assigned structure.

Sources & evidence

ORD record
ord-46d0b1599906477e95e6886d9c3ce496
Source dataset
uspto-grants-1986_06
Patent number
US04594341

Reaction notes

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