Acetic Acid → HCID 58070090, compound

HRID 2174304Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH:8]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:6].C([O-])([O-])=O.[K+].[K+].C(O)(=O)C.[CH3:39][NH:40][CH3:41]>C1COCC1.O>[CH3:39][N:40]([CH3:41])[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH:8]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[O:6]

Participants

Conditions

Temperature: 50 °C

Procedure

The Bromoacid 251 (2 mmol) is dissolved in 2M solution of dimethylamine in THF (20 mL) and to it 1 g of anhydrous K2CO3 was added and the mixture was heated in a pressure bottle at 50° C. overnight. The TLC showed the completion of the reaction. The reaction mixture was acidified with acetic acid and diluted with water (100 mL) and extracted with dichloromethane (2×60 mL). The combined organic layers were concentrated dried and used as such in the next reaction. MW calcd for C23H43NO6 429.59. Found 430.6 (MH)+. 1H NMR (400 MHz, DMSO) δ 11.87-11.82 (m, 7H), 5.75 (d, J=0.7 Hz, 15H), 4.85-4.69 (m, 38H), 3.64-3.55 (m, 12H), 3.35-2.83 (m, 106H), 3.01-2.90 (m, 59H), 2.94 (ddd, J=30.6, 7.7, 4.0 Hz, 63H), 2.90-2.73 (m, 9H), 2.70 (s, 221H), 2.57-2.46 (m, 91H), 2.44-2.30 (m, 76H), 2.17 (t, J=7.3 Hz, 147H), 1.89 (tq, J=15.5, 7.6 Hz, 88H), 1.79-1.69 (m, 13H), 1.65-1.32 (m, 311H), 1.28 (d, J=46.0 Hz, 598H).

Workup

additionwas added
customthe completion of the reaction
extractionextracted with dichloromethane (2×60 mL)
concentrationThe combined organic layers were concentrated
customdried
customsuch in the next reaction

Sources & evidence

ORD record: ord-5da4e7e9f8e64c1abad3a45f61c8f6c2
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09061063B2

Reaction notes

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