Triethylamine → HCID 67527323, compound

HRID 1840396Notes

Reaction equation

HRID 1840396 reaction equation
[C:1]([C:5]1[O:6][C:7]2[C:13]([S:14](Cl)(=[O:16])=[O:15])=[C:12]([Cl:18])[CH:11]=[CH:10][C:8]=2[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:26]([O:30][C:31](=[O:38])[NH:32][C@@H:33]1[CH2:37][CH2:36][NH:35][CH2:34]1)([CH3:29])([CH3:28])[CH3:27]>C1COCC1>[C:26]([O:30][C:31](=[O:38])[NH:32][C@@H:33]1[CH2:37][CH2:36][N:35]([S:14]([C:13]2[C:7]3[O:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[N:9][C:8]=3[CH:10]=[CH:11][C:12]=2[Cl:18])(=[O:16])=[O:15])[CH2:34]1)([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 234477912-Tert-butyl-6-chlorobenzoxazole-7-sulfonyl chloride

Product 1

HCID 67527323HCID 67527323, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure for the synthesis of sulfonylamides outlined in example 51, 2-tert-butyl-6-chloro-benzooxazole-7-sulfonyl chloride (3.0 g, 9.74 mmol), triethylamine (1.63 mL, 11.7 mmol), and (R)-pyrrolidin-3-yl-carbamic acid tert-butyl ester (2.18 g, 11.7 mmol) were reacted in THF (30 mL) to afford the title compound (3.0 g, 67%). 1H NMR (CDCl3) • 7.77 (d, 1H, J=8.5 Hz), 7.48 (d, 1H, J=8.5 Hz), 4.67 (bm, 1H), 4.22 (bm, 1H), 3.66 (bm, 2H), 3.52 (bm, 1H), 3.41 (bm, 1H), 2.19 (bm, 1H), 1.90 (bm, 1H), 1.48 (s, 9H).

Sources & evidence

ORD record
ord-d24d8048f33e42a2a2f96f9077f5076f
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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