Diethyl 2-((tert-butoxycarbonyl)amino)malonate → Diethyl 2-(tert-butoxycarbonylamino)-2-(2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethyl)malonate

HRID 1506503Notes

Reaction equation

C1(C(=NC([CH2:21][CH2:22][C:23]2[CH:24]=[C:25]3[C:48](=[CH:49][CH:50]=2)[C:29]2=[N:30][O:31][C:32]([C:33]4[C:37]([C:38]([F:41])([F:40])[F:39])=[C:36]([C:42]5[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=5)[O:35][N:34]=4)=[C:28]2[CH2:27][CH2:26]3)C(OCC)=O)C2C=CC=CC=2)C=CC=CC=1.[C:51]([O:55][C:56]([NH:58][CH:59]([C:65]([O:67][CH2:68][CH3:69])=[O:66])[C:60]([O:62][CH2:63][CH3:64])=[O:61])=[O:57])([CH3:54])([CH3:53])[CH3:52]>>[C:51]([O:55][C:56]([NH:58][C:59]([CH2:21][CH2:22][C:23]1[CH:24]=[C:25]2[C:48](=[CH:49][CH:50]=1)[C:29]1=[N:30][O:31][C:32]([C:33]3[C:37]([C:38]([F:40])([F:41])[F:39])=[C:36]([C:42]4[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=4)[O:35][N:34]=3)=[C:28]1[CH2:27][CH2:26]2)([C:60]([O:62][CH2:63][CH3:64])=[O:61])[C:65]([O:67][CH2:68][CH3:69])=[O:66])=[O:57])([CH3:54])([CH3:52])[CH3:53]

Participants

Reactant 2

HCID 382219Diethyl 2-((tert-butoxycarbonyl)amino)malonate

HCID 86669931Ethyl 2-(diphenylmethyleneamino)-4-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)butanoate

Product 1

HCID 68182047Diethyl 2-(tert-butoxycarbonylamino)-2-(2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)ethyl)malonate

Conditions

Temperature: 70 °C

Procedure

The titled compound was prepared using the experimental protocol described for Preparation 91A employing diethyl 2-(tert-butoxycarbonylamino)malonate as a starting material. The reaction was heated at 70° C. for 7 hr. The compound had an LC/MS [M-Boc]+1=584.5.

Sources & evidence

ORD record: ord-80a6909c10c6430f923a98283820f61d
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216972B2

Reaction notes

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