Methyl(2S)-2-[(22S)-8-bromo-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]-2-(tert-butoxy)acetate → Methyl(2S)-2-[(22S)-8-bromo-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]-2-(tert-butoxy)acetate

HRID 1482140Notes

Reaction equation

HRID 1482140 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.[Br:49][C:50]1[N:51]2[C:56]3[N:57]4[CH2:86][CH2:85][C:60]([CH3:87])([O:61][CH2:62][CH2:63][CH2:64][CH2:65][C@H:66]([CH3:84])[O:67][C:68]5[CH:69]=[C:70](C)[C:71]([F:82])=[CH:72][C:73]=5[C:74]5[CH:81]=[C:78]([C:79]=1[N:80]=[C:52]2[CH:53]=[C:54]([CH3:98])[C:55]=3[C@H:88]([O:93][C:94]([CH3:97])([CH3:96])[CH3:95])[C:89]([O:91][CH3:92])=[O:90])[CH:77]=[CH:76][CH:75]=5)[CH2:59][CH2:58]4>>[Br:49][C:50]1[N:51]2[C:56]3[N:57]4[CH2:58][CH2:59][C:60]([CH3:87])([O:61][CH2:62][CH2:63][CH2:64][CH2:65][C@H:66]([CH3:84])[O:67][C:68]5[CH:69]=[CH:70][C:71]([F:82])=[CH:72][C:73]=5[C:74]5[CH:81]=[C:78]([C:79]=1[N:80]=[C:52]2[CH:53]=[C:54]([CH3:98])[C:55]=3[C@H:88]([O:93][C:94]([CH3:97])([CH3:96])[CH3:95])[C:89]([O:91][CH3:92])=[O:90])[CH:77]=[CH:76][CH:75]=5)[CH2:85][CH2:86]4

Participants

3

Reactant 2

HCID 118316304Methyl(2S)-2-[(22S)-8-bromo-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]-2-(tert-butoxy)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 118316375Methyl(2S)-2-[(22S)-8-bromo-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]-2-(tert-butoxy)acetateYield 87%

Procedure

Prepared in 87.0% 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-[(22S)-8-bromo-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]-2-(tert-butoxy)acetate. LCMS (ESI, M+1): 736.3.

Sources & evidence

ORD record
ord-259d8805add24f5f9c9a1c54fe7ad64e
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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