Acetic Anhydride → HCID 49870452, compound

HRID 333898Notes

Reaction equation

HRID 333898 reaction equation
[NH2:1][C:2]1([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([C@@H:16]([N:18]3[CH2:23][CH2:22][C@:21]([CH2:30][C:31]([OH:34])([CH3:33])[CH3:32])([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[O:20][C:19]3=[O:35])[CH3:17])=[CH:12][CH:11]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.[C:45](OC(=O)C)(=[O:47])[CH3:46]>C(Cl)Cl>[OH:34][C:31]([CH3:32])([CH3:33])[CH2:30][C@@:21]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[O:20][C:19](=[O:35])[N:18]([C@H:16]([C:13]2[CH:14]=[CH:15][C:10]([C:9]#[C:8][C:2]3([NH:1][C:45](=[O:47])[CH3:46])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]3)=[CH:11][CH:12]=2)[CH3:17])[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 66869684HCID 66869684, compound

Product 1

HCID 49870452HCID 49870452, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A vial equipped with a flea stir bar was charged with (S)-3-((S)-1-(4-((1-aminocyclohexyl)ethynyl)phenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one (12 mg, 0.025 mmol), i-Pr2NEt (0.015 mL, 0.08 mmol) and CH2Cl2 (2 mL). Acetic anhydride (0.005 mL, 0.043 mmol) was added. The mixture was stirred overnight at rt and evaporated to dryness. The residue was purified by prep HPLC to afford the title compound (6.1 mg, 47%). LC-MS Method 1 tR=1.65 min, m/z=517, 459; 1H NMR (CDCl3) 1.12 (s, 3H), 1.18 (s, 3H), 1.30 (m, 1H), 1.51 (d, 3H), 1.65 (m, 6H), 1.87 (m, 2H), 1.99 (s, 3H), 2.14 (m, 3H), 2.21 (s, 2H), 2.35 (m, 1H), 2.78 (m, 1H), 5.65 (q, 1H), 6.88 (d, 2H), 7.18 (d, 2H), 7.30-7.40 (5H)

Workup

  1. customA vial equipped with a flea
  2. stirringThe mixture was stirred overnight at rt
  3. customevaporated to dryness
  4. customThe residue was purified by prep HPLC

Sources & evidence

ORD record
ord-0f67c31044264670adfa97ce230cce73
Source dataset
uspto-grants-2014_11
Patent number
US08883778B2

Reaction notes

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