Lithium Hydroxide → HCID 123320620, compound

HRID 1776098Notes

Reaction equation

HRID 1776098 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH2:15][CH2:16][C@@H:17]([C@@H:23]([O:36][Si:37]([CH:44]([CH3:46])[CH3:45])([CH:41]([CH3:43])[CH3:42])[CH:38]([CH3:40])[CH3:39])[C@@H:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=1)[CH3:25])[CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[C:10]([O:12]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>C1COCC1.O.CCOC(C)=O>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH2:15][CH2:16][C@@H:17]([C@@H:23]([O:36][Si:37]([CH:38]([CH3:40])[CH3:39])([CH:41]([CH3:43])[CH3:42])[CH:44]([CH3:46])[CH3:45])[C@@H:24]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=1)[CH3:25])[CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[C:10]([OH:12])=[O:11])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 123689953HCID 123689953, compound

Product 1

HCID 123320620HCID 123320620, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (2S,6R)-methyl 2-((tert-butoxycarbonyl)amino)-6-((1R,2S)-2-((4-methoxybenzyl)oxy)-1-((triisopropylsilyl)oxy)propyl)-9-methyldecanoate (8.76 g, 13.2 mmol) in a mixture of THF and H2O (125 mL/62.5 mL) was added LiOH (2.047 g, 85.0 mmol) and the resulting mixture was stirred for 24 h at 40° C. and then for another 24 h at room temperature. The reaction mixture was diluted with EtOAc and washed with 1.0 M aqueous HCl. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic phase was washed with brine, dried over MgSO4, and concentrated to furnish the title compound as a pale yellow oil (8.55 g, 100%): IR (neat) 2943, 2866, 1715, 1513, 1392, 1247, 1162, 1038 cm−1; 1H NMR (400 MHz, CDCl3) δ 7.26-7.20 (m, 2H), 6.88-6.82 (m, 2H), 4.96-4.83 (m, 1H), 4.51-4.31 (m, 2H), 4.31-4.20 (m, 1H), 3.88 (t, J=3.8 Hz, 1H), 3.80 (s, 3H), 3.52-3.43 (m, 1H), 1.91-1.72 (m, 2H), 1.68-1.46 (m, 5H), 1.45 (s, 9H), 1.44-1.19 (m, 2H), 1.18 (d, J=6.2 Hz, 3H), 1.18-0.98 (m, 24H), 0.86-0.80 (m, 6H); ESIMS m/z 674.6 ([M+Na]+).

Workup

  1. waitfor another 24 h at room temperature
  2. washwashed with 1.0 M aqueous HCl
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washThe combined organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1b019e7461854d2ba435d3750a8f2d88
Source dataset
uspto-grants-2016_02
Patent number
US09265253B2

Reaction notes

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