1-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acid → (1-{3-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidine-1-carbonyl}-cyclopropyl)-carbamic acid tert-butyl ester

HRID 1849009Notes

Reaction equation

HRID 1849009 reaction equation
O[C@H](C)C([N:5]1[CH2:8][CH:7]([C:9]2[CH:30]=[CH:29][C:12]3[C:13]4[N:14]=[C:15]([C:21]5[N:22]([CH:26]([CH3:28])[CH3:27])[N:23]=[CH:24][N:25]=5)[S:16][C:17]=4[CH2:18][CH2:19][O:20][C:11]=3[CH:10]=2)[CH2:6]1)=O.[C:32]([NH:39][C:40]1([C:43]([OH:45])=O)[CH2:42][CH2:41]1)([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33]>CN(C=O)C>[C:35]([O:34][C:32](=[O:33])[NH:39][C:40]1([C:43]([N:5]2[CH2:8][CH:7]([C:9]3[CH:30]=[CH:29][C:12]4[C:13]5[N:14]=[C:15]([C:21]6[N:22]([CH:26]([CH3:28])[CH3:27])[N:23]=[CH:24][N:25]=6)[S:16][C:17]=5[CH2:18][CH2:19][O:20][C:11]=4[CH:10]=3)[CH2:6]2)=[O:45])[CH2:41][CH2:42]1)([CH3:36])([CH3:37])[CH3:38]

Participants

4

Reactant 2

HCID 6883961-((tert-Butoxycarbonyl)amino)cyclopropanecarboxylic acidHCID 58204116(R)-2-hydroxy-1-{3-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidin-1-yl}-propan-1-one

Product 1

HCID 67050572(1-{3-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidine-1-carbonyl}-cyclopropyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared by a similar procedure to (R)-2-hydroxy-1-{3-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidin-1-yl}-propan-1-one using 1-(Boc-amino)cyclopropane carboxylic acid and DMF to give (1-{3-[2-(2-Isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulen-8-yl]-azetidine-1-carbonyl}-cyclopropyl)-carbamic acid tert-butyl ester isolated as a white solid (228 mg, 66%). LCMS: RT=4.72 min, [M+H]+=551

Sources & evidence

ORD record
ord-d70793edc1464450b879a86b69f10457
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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