Acetic Acid → HCID 23147259, compound

HRID 495309Notes

Reaction equation

HRID 495309 reaction equation
C(O)(=O)C.N[CH:6]([OH:12])[CH2:7][C:8]([O:10][CH3:11])=[O:9].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:27]([O:34][C:35]1[C:36]([CH2:65][CH3:66])=[C:37]([CH2:55][CH2:56][NH:57][CH:58]([OH:64])CC(OC)=O)[C:38]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[C:39]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:40]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>ClCCCl>[CH2:27]([O:34][C:35]1[C:36]([CH2:65][CH3:66])=[C:37]([CH2:55][CH2:56][N:57]2[CH:7]([C:8]([O:10][CH3:11])=[O:9])[CH2:6][O:12][C:58]2=[O:64])[C:38]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[C:39]([O:41][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH:40]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 23147199HCID 23147199, compoundHCID 23147630HCID 23147630, compound

Product 1

HCID 23147259HCID 23147259, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In the same manner as in the step 1 in Example 316, methyl 3-{2-[3,5-bis(benzyloxy)-2-ethyl-6-phenylphenyl]ethylamino}-3-hydroxypropionate was obtained from 2-[3,5-bis(benzyloxy)-2-ethyl-6-phenylphenyl]ethanal (280 mg, 0.64 mmol) obtained in the step 1 in Example 218, using acetic acid (0.6 mL), methyl 3-amino-3-hydroxypropionate (150 mg, 0.97 mmol), sodium triacetoxyborohydride (270 mg, 1.3 mmol) and 1,2-dichloroethane (6.0 mL). Then, in the same manner as in the step 2 in Example 315, methyl 3-{2-[3,5-bis(benzyloxy)-2-ethyl-6-phenylphenyl]ethyl}-2-oxo-1,3-oxazolidine-4-carboxylate (230 mg, 63%) was obtained from methyl 3-{2-[3,5-bis(benzyloxy)-2-ethyl-6-phenylphenyl]ethylamino}-3-hydroxypropionate obtained in the above.

Workup

  1. customobtained in the step 1 in Example 218

Sources & evidence

ORD record
ord-7237d605ce994d998144c59b157d6bd4
Source dataset
uspto-grants-2009_05
Patent number
US07538241B2

Reaction notes

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