methyl(2S)-2-(tert-butoxy)-2-[(22S)-5,8-dibromo-17-fluoro-4,18,22,28-tetramethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetate → Methyl(2S)-2-(tert-butoxy)-2-[(22S)-5,8-dibromo-17-fluoro-4,22,28-trimethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetate

HRID 1482056Notes

Reaction equation

HRID 1482056 reaction equation
C(O[C@@H](C1C(C)=CC2=NC3=CN2C=1N1CCC(C)(OCCCC[C@H](C)OC2C=CC(F)=CC=2C2C=C3C=CC=2)CC1)C(OC)=O)(C)(C)C.[C:49]([O:53][C@@H:54]([C:59]1[C:88]([CH3:89])=[C:87]([Br:90])[C:86]2=[N:91][C:83]3=[C:84]([Br:92])[N:85]2[C:60]=1[N:61]1[CH2:98][CH2:97][C:64]([CH3:99])([O:65][CH2:66][CH2:67][CH2:68][CH2:69][C@H:70]([CH3:96])[O:71][C:72]2[CH:73]=[C:74](C)[C:75]([F:94])=[CH:76][C:77]=2[C:78]2[CH:93]=[C:82]3[CH:81]=[CH:80][CH:79]=2)[CH2:63][CH2:62]1)[C:55]([O:57][CH3:58])=[O:56])([CH3:52])([CH3:51])[CH3:50]>>[C:49]([O:53][C@@H:54]([C:59]1[C:88]([CH3:89])=[C:87]([Br:90])[C:86]2=[N:91][C:83]3=[C:84]([Br:92])[N:85]2[C:60]=1[N:61]1[CH2:62][CH2:63][C:64]([CH3:99])([O:65][CH2:66][CH2:67][CH2:68][CH2:69][C@H:70]([CH3:96])[O:71][C:72]2[CH:73]=[CH:74][C:75]([F:94])=[CH:76][C:77]=2[C:78]2[CH:93]=[C:82]3[CH:81]=[CH:80][CH:79]=2)[CH2:97][CH2:98]1)[C:55]([O:57][CH3:58])=[O:56])([CH3:52])([CH3:50])[CH3:51]

Participants

3

Reactant 2

HCID 118316307methyl(2S)-2-(tert-butoxy)-2-[(22S)-5,8-dibromo-17-fluoro-4,18,22,28-tetramethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetateHCID 131736666methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-4,22,28-trimethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetate

Product 1

HCID 118316310Methyl(2S)-2-(tert-butoxy)-2-[(22S)-5,8-dibromo-17-fluoro-4,22,28-trimethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetateYield 73%

Procedure

Prepared in 73% yield from methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-4,22,28-trimethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetate following the procedure for methyl(2S)-2-(tert-butoxy)-2-[(22S)-5,8-dibromo-17-fluoro-4,18,22,28-tetramethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetate. LCMS (ESI, M+1): 816.05.

Sources & evidence

ORD record
ord-b302559841784ceba8db1e3f5ae495d3
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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