Methyl(2S)-2-[(22S)-5-acetyl-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 → (2S)-2-[(22S)-5-Acetyl-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)acetic acid

HRID 1482148Notes

Reaction equation

HRID 1482148 reaction equation
[C:1]([C:4]1[C:33]2=[N:34][C:30]3=[CH:31][N:32]2[C:7]([N:8]2[CH2:39][CH2:38][C:11]([CH3:40])([O:12][CH2:13][CH2:14][CH2:15][CH2:16][C@H:17]([CH3:37])[O:18][C:19]4[CH:20]=[CH:21][C:22]([F:36])=[CH:23][C:24]=4[C:25]4[CH:35]=[C:29]3[CH:28]=[CH:27][CH:26]=4)[CH2:10][CH2:9]2)=[C:6]([C@H:41]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])[C:42]([O:44]C)=[O:43])[C:5]=1[CH3:51])(=[O:3])[CH3:2].C(O[C@@H](C1C(C)=CC2=NC3=C(Cl)N2C=1N1CCC(C)(OCCCC[C@H](C)OC2C=CC(C)=CC=2C2C=C3C=CC=2)CC1)C(O)=O)(C)(C)C>>[C:1]([C:4]1[C:33]2=[N:34][C:30]3=[CH:31][N:32]2[C:7]([N:8]2[CH2:9][CH2:10][C:11]([CH3:40])([O:12][CH2:13][CH2:14][CH2:15][CH2:16][C@H:17]([CH3:37])[O:18][C:19]4[CH:20]=[CH:21][C:22]([F:36])=[CH:23][C:24]=4[C:25]4[CH:35]=[C:29]3[CH:28]=[CH:27][CH:26]=4)[CH2:38][CH2:39]2)=[C:6]([C@H:41]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])[C:42]([OH:44])=[O:43])[C:5]=1[CH3:51])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 118316383Methyl(2S)-2-[(22S)-5-acetyl-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)acetateHCID 118332041(2S)-2-(tert-Butoxy)-2-[(22S)-8-chloro-4,17,22,28-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]acetic acid

Product 1

HCID 118316384(2S)-2-[(22S)-5-Acetyl-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)acetic acidYield 4.3%

Procedure

Prepared in 4.3% yield from methyl(2S)-2-[(22S)-5-acetyl-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 following the procedure for (2S)-2-(tert-butoxy)-2-[(22S)-8-chloro-4,17,22,28-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]acetic acid. 1H NMR (500 MHz, DMSO-d6) δ 8.16 (s, 1H), 8.09 (d, J=7.7 Hz, 1H), 8.03 (s, 1H), 7.53 (t, J=7.5 Hz, 1H), 7.36 (d, J=7.7 Hz, 1H), 7.23-7.13 (m, 3H), 5.85 (br. s., 1H), 4.61 (br. s., 1H), 3.87-3.79 (m, 1H), 3.63-3.55 (m, 1H), 3.45 (br. s., 3H), 3.33 (br. s., 1H), 2.76 (s, 3H), 2.67 (d, J=8.1 Hz, 1H), 2.28 (s, 3H), 1.89-1.61 (m, 9H), 1.51 (br. s., 1H), 1.19 (s, 3H), 1.15 (s, 9H), 1.06 (d, J=5.9 Hz, 3H); LCMS (ESI, M+1): 686.4.

Sources & evidence

ORD record
ord-f19fd24cbcc448cc90067a9a32552f35
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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