Ammonium Chloride → HCID 53863200, compound

HRID 1492948Notes

Reaction equation

HRID 1492948 reaction equation
[CH2:1]([CH:4]1[CH:30]=[C:29]([CH3:31])[CH2:28][CH:27]([CH3:32])[CH2:26][CH:25]([O:33][CH3:34])[CH:24]2[O:35][C:20]([OH:39])([CH:21]([CH3:38])[CH2:22][CH:23]2[O:36][CH3:37])[C:19](=[O:40])[C:18](=[O:41])[N:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:11](=[O:42])[O:10][CH:9]([C:43]([CH3:54])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([OH:51])[CH:47]([O:52][CH3:53])[CH2:46]2)[CH:8]([CH3:55])[CH:7]=[CH:6][C:5]1=[O:56])[CH:2]=[CH2:3].CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].[Cl-].[NH4+]>O1CCCC1.C(O)(C)(C)C>[CH2:1]([CH:4]1[CH:30]=[C:29]([CH3:31])[CH2:28][CH:27]([CH3:32])[CH2:26][CH:25]([O:33][CH3:34])[CH:24]2[O:35][C:20]([OH:39])([CH:21]([CH3:38])[CH2:22][CH:23]2[O:36][CH3:37])[C:19](=[O:40])[C:18](=[O:41])[N:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[C:11](=[O:42])[O:10][CH:9]([C:43]([CH3:54])=[CH:44][CH:45]2[CH2:50][CH2:49][CH:48]([OH:51])[CH:47]([O:52][CH3:53])[CH2:46]2)[CH:8]([CH3:55])[CH:7]=[CH:6][CH:5]1[OH:56])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 3611392Lithium tri-s-butylborohydrideHCID 5715345717-Allyl-1-hydroxy-12-[2-(4-hydroxy-3-methoxycyclohexyl)-1-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacosa-14,18-diene-2,3,10,16-tetraone

Product 1

HCID 53863200HCID 53863200, compoundYield 19.9%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The title compound from example 14 (50 mg) was dissolved in tetrahydrofuran (3 ml) and t-butanol (0.05 ml). The resulting solution was added dropwise to a stirred solution of L-Selectride (Registered Trade Mark) (0.3 ml of a 1M solution in tetrahydrofuran) under a nitrogen atmosphere at -78° C. Stirring was continued for 40 minutes, after which saturated ammonium chloride solution (5 ml) was added and the mixture extracted with ethyl acetate. After filtration of the organic phase, and removal of solvent in vacuo, chromatography on silica eluting with ether/methanol (15:1) yielded the title compound as an oil (10 mg).

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. filtrationAfter filtration of the organic phase, and removal of solvent in vacuo, chromatography on silica eluting with ether/methanol (15:1)

Sources & evidence

ORD record
ord-c4e426aa49894139ae185a5500eff18d
Source dataset
uspto-grants-1994_12
Patent number
US05376663

Reaction notes

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