O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → (4-{[methyl-((R)-tetrahydro-furan-2-carbonyl)-amino]-methyl}-thiazol-2-yl)-carbamic acid tert-butyl ester

HRID 1685068Notes

Reaction equation

HRID 1685068 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[N:5]=[C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[S:7][CH:8]=1.[O:17]1[CH2:21][CH2:20][CH2:19][C@@H:18]1[C:22]([OH:24])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>>[C:12]([O:11][C:10](=[O:16])[NH:9][C:6]1[S:7][CH:8]=[C:4]([CH2:3][N:2]([CH3:1])[C:22]([C@H:18]2[CH2:19][CH2:20][CH2:21][O:17]2)=[O:24])[N:5]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2734707Tetrahydro-2-furoic acid, (+)-HCID 58055063tert-Butyl (4-((methylamino)methyl)thiazol-2-yl)carbamate2×

Product 1

HCID 86661307(4-{[methyl-((R)-tetrahydro-furan-2-carbonyl)-amino]-methyl}-thiazol-2-yl)-carbamic acid tert-butyl ester

Procedure

tert-Butyl 4-((methylamino)methyl)thiazol-2-ylcarbamate (Intermediate 17) was coupled with (R)-2-tetrahydrofuroic acid using TBTU (Method 2) to afford (4-{[methyl-((R)-tetrahydro-furan-2-carbonyl)-amino]-methyl}-thiazol-2-yl)-carbamic acid tert-butyl ester.

Sources & evidence

ORD record
ord-d881abefa4e245138c951ae14428bed0
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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