Sodium Hydroxide → HCID 73387236, compound

HRID 1400705Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:11]1[C:42]([CH3:43])=[N:41][C:40]2=[CH:44][C:37]3=[N:38][N:39]2[C:12]=1[C:13]1[CH:47]=[C:46]2[C:16]([O:17][CH2:18][CH2:19][N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=2[C:32]2[CH:45]=[C:36]3[CH:35]=[CH:34][CH:33]=2)=[CH:15][C:14]=1[F:48])[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C@@H:6]([C:11]1[C:42]([CH3:43])=[N:41][C:40]2=[CH:44][C:37]3=[N:38][N:39]2[C:12]=1[C:13]1[CH:47]=[C:46]2[C:16]([O:17][CH2:18][CH2:19][N:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=2[C:32]2[CH:45]=[C:36]3[CH:35]=[CH:34][CH:33]=2)=[CH:15][C:14]=1[F:48])[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of methyl (2S)-2-(tert-butoxy)-2-{32-fluoro-4-methyl-29-oxa-5,7,8,26-tetraazaheptacyclo[24.6.2.16,9.110,14.02,7.015,20.030,34]hexatriaconta-1(32),2,4,6(36),8,10(35),11,13,15(20),16,18,30,33-tridecaen-3-yl}acetate (0.023 g, 0.036 mmol) in MeOH (˜2 mL) was treated with 1.0 N aq. NaOH (0.360 ml, 0.360 mmol) and heated (70° C. oil bath) for 4 h, then temperature was lowered to 50° C. and stirring continued for 16 h. The reaction was cooled and purified by prep-HPLC to afford desired product. 1H NMR (500 MHz, DMSO-d6) δ 7.98-7.83 (m, 2H), 7.59-7.49 (m, 1H), 7.40-7.29 (m, 2H), 7.29-7.20 (m, 2H), 7.17 (br. s., 2H), 7.00 (d, J=6.4 Hz, 1H), 6.82 (d, J=10.4 Hz, 1H), 4.84 (br. s., 1H), 4.19 (br. s., 3H), 2.94-2.79 (m, 2H), 2.72 (d, J=12.2 Hz, 2H), 2.62 (br. s., 3H), 1.69 (br. s., 1H), 1.59-1.18 (m, 6H), 0.92 (br. s., 9H). UPLC-MS (M+H)=635.4.

Workup

customwas lowered to 50° C.
temperatureThe reaction was cooled
custompurified by prep-HPLC

Sources & evidence

ORD record: ord-a05ce59aabae4e57828ab4fd4cdc0953
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906929B2

Reaction notes

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