Hydrochloric Acid → HCID 21844872, compound

HRID 618913Notes

Reaction equation

HRID 618913 reaction equation
[C:1]([CH2:4][N:5]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12][N:11]([CH2:17][C:18]([OH:20])=[O:19])[CH2:10][CH2:9][N:8]([CH:21]([CH2:25][CH2:26][CH:27]([N:31]2[CH2:42][CH2:41][N:40]([CH2:43][C:44]([OH:46])=[O:45])[CH2:39][CH2:38][NH:37][CH2:36][CH2:35][N:34]([CH2:47][C:48]([OH:50])=[O:49])[CH2:33][CH2:32]2)[C:28]([OH:30])=[O:29])[C:22]([OH:24])=[O:23])[CH2:7][CH2:6]1)([OH:3])=[O:2].[Li+].[OH-:52].CC1(C)[O:61][CH2:60][CH:59]2[CH:57]([O:58]2)[CH2:56][O:55]1.Cl>O>[OH:52][CH2:60][CH:59]([N:37]1[CH2:36][CH2:35][N:34]([CH2:47][C:48]([OH:50])=[O:49])[CH2:33][CH2:32][N:31]([CH:27]([CH2:26][CH2:25][CH:21]([N:8]2[CH2:7][CH2:6][N:5]([CH2:4][C:1]([OH:3])=[O:2])[CH2:16][CH2:15][N:14]([CH:57]([CH2:56][OH:55])[CH:59]([OH:58])[CH2:60][OH:61])[CH2:13][CH2:12][N:11]([CH2:17][C:18]([OH:20])=[O:19])[CH2:10][CH2:9]2)[C:22]([OH:24])=[O:23])[C:28]([OH:30])=[O:29])[CH2:42][CH2:41][N:40]([CH2:43][C:44]([OH:46])=[O:45])[CH2:39][CH2:38]1)[CH:57]([OH:58])[CH2:56][OH:55]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 110947474,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octaneHCID 21844869HCID 21844869, compound

Product 1

HCID 21844872HCID 21844872, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

The amine of Example 5 (500 mg, 0.70mmol) was dissolved in water (20 mL), and the pH was adjusted to 11.5 with 1M LiOH. The reaction mixture was heated at 60° C., and three aliquots of 4,4-dimethyl-3,5,8-trioxabicyclo[5.1.0]octane (see J. Org. Chem. 41: 2469 (1976)) (180 μL) were added at 8 hour intervals. Heating was continued for 48 hours. After cooling, the mixture was treated with 10% HCl, refluxed for 2 hours, and loaded on an AG1-X8 cation exchange column [40 mL (OAc form)]. The column was washed with water (500 mL), and the product was eluted with 1M CH2COOH. The fractions containing the product were combined and evaporated to a white powder (420 mg (81.4%)). 1H NMR (D2O, 355° K) δ 1.6-2.0 (br mult., 4H), 2.7-3.8 (br mult. 54H). 13C NMR (D2O): 23.5, 25.2, 25.5, 44.5, 44.9, 49.8, 50.3, 54.9, 55.1, 57.2, 58.0, 58.7, 59.5, 61.6, 62.2, 62.9, 68.6, 69.1, 169.6, 170.2, 174.0. MS (FAB): m/e 927.5 (MH+). Anal. Calcd for C38H70N8O18 8H2O: C, 43.92; H, 8.34; N, 10.78. Found C, 43.94; H, 7.65; N, 10.78.

Workup

  1. temperatureHeating
  2. temperatureAfter cooling
  3. temperaturerefluxed for 2 hours
  4. washThe column was washed with water (500 mL)
  5. washthe product was eluted with 1M CH2COOH
  6. additionThe fractions containing the product
  7. customevaporated to a white powder (420 mg (81.4%))

Sources & evidence

ORD record
ord-40a70b93b5444d1eabfbe90179f1280b
Source dataset
uspto-grants-1999_09
Patent number
US05958373

Reaction notes

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