Acetyl chloride → HCID 6321073, compound

HRID 1253958Notes

Reaction equation

HRID 1253958 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:44]=[CH:43][C:8]([CH2:9][C@H:10]([NH:31][C:32](=[O:42])[O:33][C@@H:34]2[C@H:41]3[C@H:37]([O:38][CH2:39][CH2:40]3)[O:36][CH2:35]2)[C@H:11]([OH:30])[CH2:12][N:13]([S:18]([C:21]2[CH:29]=[CH:28][C:24]3[O:25][CH2:26][O:27][C:23]=3[CH:22]=2)(=[O:20])=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:7][CH:6]=1.C(N(CC)C(C)C)(C)C.[C:54](Cl)(=[O:56])[CH3:55]>C1COCC1.C(Cl)Cl>[C:54]([NH:1][CH2:2][CH2:3][O:4][C:5]1[CH:44]=[CH:43][C:8]([CH2:9][C@H:10]([NH:31][C:32](=[O:42])[O:33][C@@H:34]2[C@H:41]3[C@H:37]([O:38][CH2:39][CH2:40]3)[O:36][CH2:35]2)[C@H:11]([OH:30])[CH2:12][N:13]([S:18]([C:21]2[CH:29]=[CH:28][C:24]3[O:25][CH2:26][O:27][C:23]=3[CH:22]=2)(=[O:19])=[O:20])[CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:7][CH:6]=1)(=[O:56])[CH3:55]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 6321070HCID 6321070, compound

Product 1

HCID 6321073HCID 6321073, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

A solution of 21 mg (0.033 mmol) of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-1-[4-(2-aminoethoxy)benzyl]-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxypropylcarbamate in 2 mL of 1:1 THF/CH2Cl2 was treated with 9 μL (0.050 mmol) of N,N-diisopropylethylamine followed by 2.6 mL (0.036 mmol) of acetyl chloride. The resulting solution was stirred at RT. After 1.5 hours the solution was concentrated in vacuo and the residue subjected to flash chromatography (SiO2, 95:5 CH2Cl2/MeOH) to afford the desired compound in 86% yield as a white foam. 1H NMR (CDCl3): 7.29 (dd, 1H), 7.16-7.04 (m, 3H), 7.05 (d, 1H), 6.76 (d, 2H), 6.05 (s, 2H), 5.91 (br s, 1H), 5.01 (d, 1H), 5.05-4.89 (m, 2H), 3.94 (m, 3H), 3.80 (m, 3H), 3.72-3.51 (m, 5H), 3.08 (dd, 1H), 3.01-2.83 (m, 4H), 2.74 (m, 2H), 1.97 (s, 3H), 1.86-1.45 (m, 3H), 0.90 (d, 3H), 0.84 (d, 3H). MS(ESI): 678(M+H).

Workup

  1. concentrationAfter 1.5 hours the solution was concentrated in vacuo

Sources & evidence

ORD record
ord-ca5da9031292407faf71099f4e4acedd
Source dataset
uspto-grants-2013_06
Patent number
US08455497B2

Reaction notes

Loading…