Triphenylphosphine → N-(Triphenylmethyl)-O-[4-[6-benzyloxy-3-[3-methoxy-4-[(1-pyrrolidinyl)methyl]benzyl]benzo[b]thiophen-2-yl]phenyl]-L-serine methyl ester

HRID 1387096Notes

Reaction equation

HRID 1387096 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:16]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[C:20]([O:30][CH3:31])[CH:19]=3)=[C:15]([C:32]3[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=3)[S:14][C:13]=2[CH:39]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:59][O:60][C:61](=[O:85])[C@H:62]([CH2:83]O)[NH:63][C:64]([C:77]1[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=1)([C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1)[C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.CCN(CC)CC.CO.CCOC(C)=O.CCOC(C)=O>[CH3:59][O:60][C:61](=[O:85])[C@H:62]([CH2:83][O:38][C:35]1[CH:36]=[CH:37][C:32]([C:15]2[S:14][C:13]3[CH:39]=[C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:10]=[CH:11][C:12]=3[C:16]=2[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[C:20]([O:30][CH3:31])[CH:19]=2)=[CH:33][CH:34]=1)[NH:63][C:64]([C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1)([C:65]1[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=1)[C:77]1[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=1

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 7128367N-(Triphenylmethyl)-L-serine methyl esterHCID 22462686HCID 22462686, compound

Product 1

HCID 70093768N-(Triphenylmethyl)-O-[4-[6-benzyloxy-3-[3-methoxy-4-[(1-pyrrolidinyl)methyl]benzyl]benzo[b]thiophen-2-yl]phenyl]-L-serine methyl esterYield 28%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 21980445Ethyl acetate methanol triethylamineSolvent

Procedure

To a stirring solution of 6-benzyloxy-2-(4-hydroxyphenyl)-[3-methoxy-4-[(1-pyrrolidinyl)methyl]benzyl]benzo[b]thiophene (359 mg, 0.67 mmol), triphenylphosphine (300 mg) and N-trityl-L-serine methyl ester (392 mg) in THF (6 mL) at 0° C. was added diethyl azodicarboxylate (0.18 mL) over 5 min. The mixture was stirred at ambient temperature under argon for 24 h before concentration under reduced pressure. Chromatography with EtOAc followed by Et3N:MeOH:EtOAc (5:5:90) afforded the product (165 mg, 19%).

Sources & evidence

ORD record
ord-de12e4313ba744d790ecfa332c3a678a
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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