Methanol → (2S)-2-(tert-Butoxy)-2-[4,23-dimethyl-22-oxa-1,5,7,8-tetraazapentacyclo[21.2.2.16,9.02,7.013,18]octacosa-2,4,6(28),8,10,13(18),14,16,19-nonaen-3-yl]acetic acid

HRID 921105Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:12]1[C:36]([CH3:37])=[N:35][C:34]2=[CH:38][C:31]3=[N:32][N:33]2[C:13]=1[N:14]1[CH2:40][CH2:39][C:17]([CH3:41])([O:18][CH2:19][CH:20]=[CH:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=2[CH2:28][CH:29]=[CH:30]3)[CH2:16][CH2:15]1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[Na+]>O1CCOCC1>[C:1]([O:5][C@@H:6]([C:12]1[C:36]([CH3:37])=[N:35][C:34]2=[CH:38][C:31]3=[N:32][N:33]2[C:13]=1[N:14]1[CH2:15][CH2:16][C:17]([CH3:41])([O:18][CH2:19][CH:20]=[CH:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=2[CH2:28][CH:29]=[CH:30]3)[CH2:39][CH2:40]1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of the ethyl (2S)-2-(tert-butoxy)-2-[4,23-dimethyl-22-oxa-1,5,7,8-tetraazapentacyclo[21.2.2.16,9.02,7.013,18]octacosa-2,4,6(28),8,10,13(18),14,16,19-nonaen-3-yl]acetate (0.0366 g, 0.066 mmol)) in dioxane (1 mL)/MeOH (1 mL) was added 10N sodium hydroxide (0.066 mL, 0.655 mmol) and the mixture was stirred at 70° C. for 1 h. The reaction was cooled and concentrated. The crude material was purified via preparative HPLC to give the title compound as diastereomers. LCMS (M+H) calcd for C31H38N4O4: 531.29. found: 531.4.

Workup

temperatureThe reaction was cooled
concentrationconcentrated
customThe crude material was purified via preparative HPLC

Sources & evidence

ORD record: ord-b5b8de3b087c485a898cac89c7c473f1
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273067B2

Reaction notes

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