Methyl(2S)-2-(tert-butoxy)-2-[(22S)-16,17-difluoro-5-(1-hydroxyethyl)-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 → Methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-5-(1-hydroxyethyl)-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 1482121Notes

Reaction equation

C(O[C@@H](C1C(C)=C(C=O)C2=NC3=CN2C=1N1CCC(C)(OCCCC[C@H](C)OC2C=CC(F)=CC=2C2C=C3C=CC=2)CC1)C(OC)=O)(C)(C)C.[C:51]([O:55][C@@H:56]([C:61]1[C:90]([CH3:91])=[C:89]([CH:92]([OH:94])[CH3:93])[C:88]2=[N:95][C:85]3=[CH:86][N:87]2[C:62]=1[N:63]1[CH2:101][CH2:100][C:66]([CH3:102])([O:67][CH2:68][CH2:69][CH2:70][CH2:71][C@H:72]([CH3:99])[O:73][C:74]2[CH:75]=[CH:76][C:77]([F:98])=[C:78](F)[C:79]=2[C:80]2[CH:96]=[C:84]3[CH:83]=[CH:82][CH:81]=2)[CH2:65][CH2:64]1)[C:57]([O:59][CH3:60])=[O:58])([CH3:54])([CH3:53])[CH3:52]>>[C:51]([O:55][C@@H:56]([C:61]1[C:90]([CH3:91])=[C:89]([CH:92]([OH:94])[CH3:93])[C:88]2=[N:95][C:85]3=[CH:86][N:87]2[C:62]=1[N:63]1[CH2:64][CH2:65][C:66]([CH3:102])([O:67][CH2:68][CH2:69][CH2:70][CH2:71][C@H:72]([CH3:99])[O:73][C:74]2[CH:75]=[CH:76][C:77]([F:98])=[CH:78][C:79]=2[C:80]2[CH:96]=[C:84]3[CH:83]=[CH:82][CH:81]=2)[CH2:100][CH2:101]1)[C:57]([O:59][CH3:60])=[O:58])([CH3:52])([CH3:53])[CH3:54]

Participants

Reactant 2

HCID 118316353Methyl(2S)-2-(tert-butoxy)-2-[(22S)-16,17-difluoro-5-(1-hydroxyethyl)-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

HCID 118316355Methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-5-formyl-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 118316356Methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-5-(1-hydroxyethyl)-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 46.9%

Procedure

Prepared in 46.9% yield from methyl(2S)-2-(tert-butoxy)-2-[(22S)-17-fluoro-5-formyl-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)-16,17-difluoro-5-(1-hydroxyethyl)-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. LCMS (ESI, M+1): 702.4.

Sources & evidence

ORD record: ord-ee0ad2489e3f45019bee6e08d56c805b
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409922B2

Reaction notes

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