Hydrochloric Acid → HCID 86762374, compound

HRID 1470903Notes

Reaction equation

HRID 1470903 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]1[C:17]([C:48]([NH:50][CH2:51][CH:52]2[CH2:56][O:55]C(C)(C)[O:53]2)=[O:49])=[N:18][C:19]([NH:33][CH2:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][O:46][CH3:47])=[C:20]([C:22]([NH:24][CH2:25][CH:26]2[CH2:30][O:29]C(C)(C)[O:27]2)=[O:23])[N:21]=1.Cl>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]1[C:17]([C:48]([NH:50][CH2:51][CH:52]([OH:53])[CH2:56][OH:55])=[O:49])=[N:18][C:19]([NH:33][CH2:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][O:40][CH2:41][CH2:42][O:43][CH2:44][CH2:45][O:46][CH3:47])=[C:20]([C:22]([NH:24][CH2:25][CH:26]([OH:27])[CH2:30][OH:29])=[O:23])[N:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86762375HCID 86762375, compound

Product 1

HCID 86762374HCID 86762374, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a reddish solution of the above dicetonide 14 (1.00 mmol) in THF (25 mL), was added 1.0 N HCl (5 mL) and stirred for 5 h in an atmosphere of argon. Most of the THF was removed from the reaction mixture, neutralized by 1.0 N NaOH, and concentrated in vacuo. The crude product (2.40 g) was subjected to preparative RP-HPLC (XBridge, 10-50% B/12 min) to afford diastereomeric 13 (0.554 g, 74%) as red gum: UV (λmax) 499 nm; 1H NMR (CDCl3) 8.66, 8.56 (2 t, 2), 6.24 (broad s, 6), 4.40 (t, 1.5, J=4.2, 5.2), 4.23-4.15 (m, 1.5), 3.97-3.90 (m, 3), 3.70-3.50 (m, 36), 3.37, 3.36 (2 s, 6), 1.98-1.90 (quintet, 4); RP-HPLC (254 nm) 98% (tR=17.43 min, 5-50% B); RP-LC/MS (ESI) m/z 754.5 (M+H)+ (tR=3.58 min). HRMS (ESI) m/z calculated for C32H51N6O14 (M+H)+ 753.4240, found 753.4252.

Workup

  1. customMost of the THF was removed from the reaction mixture
  2. concentrationconcentrated in vacuo
  3. customwas subjected to preparative RP-HPLC (XBridge, 10-50% B/12 min)

Sources & evidence

ORD record
ord-9f2da03ce0dd462b81cf76cc49045870
Source dataset
uspto-grants-2015_04
Patent number
US09005581B2

Reaction notes

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