Diisopropylethylamine → (+)-1-Oxa-8-aza-spiro [4.5]decane-8-carboxylic acid (7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-amide

HRID 985868Notes

Reaction equation

HRID 985868 reaction equation
C1(O[C:8](=[O:27])[NH:9][C:10]2[S:11][C:12]3[C:18]([CH:19]4[CH2:24][O:23][CH2:22][CH2:21][O:20]4)=[CH:17][CH:16]=[C:15]([O:25][CH3:26])[C:13]=3[N:14]=2)C=CC=CC=1.FC(F)(F)C(O)=O.[O:35]1[C:39]2([CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)[CH2:38][CH2:37][CH2:36]1.C(N(C(C)C)C(C)C)C>C(Cl)(Cl)Cl>[O:20]1[CH2:21][CH2:22][O:23][CH2:24][CH:19]1[C:18]1[C:12]2[S:11][C:10]([NH:9][C:8]([N:42]3[CH2:43][CH2:44][C:39]4([O:35][CH2:36][CH2:37][CH2:38]4)[CH2:40][CH2:41]3)=[O:27])=[N:14][C:13]=2[C:15]([O:25][CH3:26])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 20769454(+)-(7-[1,4]Dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-carbamic acid phenyl esterHCID 225077071-Oxa-8-azaspiro[4.5]decane, trifluoroacetate (9CI)

Product 1

HCID 86594662(+)-1-Oxa-8-aza-spiro [4.5]decane-8-carboxylic acid (7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-amide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

From (+)-(7-[1,4]dioxan-2-yl-4-methoxy-benzothiazol-2-yl)-carbamic acid phenyl ester with 1-oxa-8-aza-spiro[4.5]decane trifluoroacetate and N-ethyldiisopropylamine in chloroform. [α]D20=+25.8° (c=1.01, CHCl3), ES-MS m/e (%): 434 (M+H+, 100).

Sources & evidence

ORD record
ord-a2d64ea76e0b413ab294ac5820037057
Source dataset
uspto-grants-2005_03
Patent number
US06872833B2

Reaction notes

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