Diisopropylethylamine → HCID 118379460, compound

HRID 708440Notes

Reaction equation

HRID 708440 reaction equation
OC(C(F)(F)F)=O.[NH2:8][CH2:9][C:10]1[CH:14]=[N:13][N:12]([CH2:15][C@@H:16]2[C@H:19]([NH:20][C:21](=[O:37])/[C:22](=[N:29]\[O:30][C:31]([CH3:36])([CH3:35])[C:32]([OH:34])=[O:33])/[C:23]3[N:24]=[C:25]([NH2:28])[S:26][CH:27]=3)[C:18](=[O:38])[N:17]2[S:39]([OH:42])(=[O:41])=[O:40])[N:11]=1.Cl[S:44]([NH:47]C(=O)OC(C)(C)C)(=[O:46])=[O:45].CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:28][C:25]1[S:26][CH:27]=[C:23](/[C:22](=[N:29]/[O:30][C:31]([CH3:36])([CH3:35])[C:32]([OH:34])=[O:33])/[C:21](=[O:37])[NH:20][C@H:19]2[C@@H:16]([CH2:15][N:12]3[N:11]=[C:10]([CH2:9][NH:8][S:44](=[O:46])(=[O:45])[NH2:47])[CH:14]=[N:13]3)[N:17]([S:39]([OH:42])(=[O:41])=[O:40])[C:18]2=[O:38])[N:24]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 15677406tert-butyl N-(chlorosulfonyl)carbamateHCID 178460222HCID 178460222, compound

Product 1

HCID 118379460HCID 118379460, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared in an analogous manner to example 53, using 2-(((Z)-(2-(((2R,3S)-2-((4-(aminomethyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxo-1-sulfoazetidin-3-yl)amino)-1-(2-aminothiazol-4-yl)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid TFA salt, crude compound (200 mg, 0.318 mmol), tert-butyl chlorosulfonylcarbamate (68 mg, 0.318 mmol), DIPEA (113 mL, 0.636 mmol) and DMF (1 mL). LCMS: m/z=609.1 (M−1). 1H NMR (400 MHz, D2O): δ 7.65 (s, 1H), 6.98 (s, 1H), 5.40 (d, J=6.0 Hz, 1H), 4.85-4.83 (m, 1H), 4.76-4.74 (m, 2H), 4.13 (s, 2H), 1.26 (s, 3H), 1.25 (s, 3H).

Workup

  1. customPrepared in an analogous manner to example 53

Sources & evidence

ORD record
ord-b12ac3d5864042d18d0062b8d01b6c73
Source dataset
uspto-grants-2015_11
Patent number
US09174978B2

Reaction notes

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