Hydrochloric Acid → Ceramide NG

HRID 222841Notes

Reaction equation

[C:1]([NH:20][C@H:21]([C@H:27]([OH:43])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:22](OCC)=[O:23])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[BH4-].[Na+].[Cl-].[Ca+2].[Cl-].Cl>O.C1COCC1>[C:1]([NH:20][C@H:21]([C@H:27]([OH:43])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:22][OH:23])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

Conditions

Temperature: 50 °C

Procedure

Ethyl (2R,3R)-2-octadecanoylamino-3-hydroxyoctadecanoate (5.00 g, 8.17 mmol) synthesized in the same manner as Example 17 was added to a THF suspension (48 mL) containing sodium borohydride (0.62 mg, 16.34 mmol) at 0° C. for 5 hour. After completion of the dropwise addition, calcium chloride (1.82 mg, 16.40 mmol) was added for 1 hour. After water was added to the reaction mixture, concentrated hydrochloric acid was added thereto to adjust pH of the mixture to be 1.5. The mixture was further stirred at 50° C. for 1 hour, and the organic layer was separated. It was confirmed by comparative analysis of the organic layer with sample product using HPLC that the organic layer contained 4.41 g of the title compound (yield: 95%). It was also found that anti-form:syn-form was 98:2 and the optical purity of the anti-form was 99% ee.

Workup

additionwas added for 1 hour
additionwas added
customthe organic layer was separated

Sources & evidence

ORD record: ord-94bdba413a8a4b579fa64e74f5b7b5e8
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207370B2

Reaction notes

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