Water → HCID 13432890, compound

HRID 2088859Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([N:26]1[CH2:33][CH2:32][CH2:31][C@@H:27]1[C:28]([NH2:30])=O)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[C:7]([N:26]1[CH2:33][CH2:32][CH2:31][C@@H:27]1[CH2:28][NH2:30])([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Under cold conditions (ice bath) and under an inert atmosphere, 60 ml (61.6 mmol) of a solution of lithium aluminium hydride (1N) in THF are added dropwise to 11 g (30.8 mmol) of the compound obtained from step 1.8 suspended in THF (60 ml). After addition, the reaction mixture is heated for 3 hours at 70° C. and then cooled to 0° C. 2.8 ml of water (formation of a precipitate), 2.8 ml of NaOH solution (1N) and 8.3 ml of water are then successively added dropwise. This mixture is stirred for 30 minutes and then filtered, the solid is rinsed with THF (10 ml) and the filtrate is then concentrated under reduced pressure. 10 g of compound are obtained in the form of a bright yellow powder, which is used without further purification in the following step. Yield=95%. Melting point: 100° C.

Workup

additionAfter addition
temperaturecooled to 0° C
filtrationfiltered
washthe solid is rinsed with THF (10 ml)
concentrationthe filtrate is then concentrated under reduced pressure

Sources & evidence

ORD record: ord-99ff8a592a6b4b4b9cffefaf2d734cbc
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436011B2

Reaction notes

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