Tributyltin Chloride → HCID 131717967, compound

HRID 1587261Notes

Reaction equation

HRID 1587261 reaction equation
[C:1]([NH:11][C@H:12]([C:21]([OH:23])=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][C:17](Cl)=[CH:16][CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C([Li])CCC.[Sn:29](Cl)([CH2:38][CH2:39][CH2:40][CH3:41])([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH2:32][CH3:33]>C1COCC1>[C:1]([NH:11][C@H:12]([C:21]([OH:23])=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Sn:29]([CH2:34][CH2:35][CH2:36][CH3:37])([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:30][CH2:31][CH2:32][CH3:33])=[CH:16][CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

5

Reactant 3

HCID 15096Tributyltin Chloride2×HCID 3033106(S)-2-(((Benzyloxy)carbonyl)amino)-3-(4-chlorophenyl)propanoic acidHCID 178418339Butyllithium

Product 1

HCID 131717967HCID 131717967, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-CBZ p-chloro phenylalanine 1 (one equivalent) in anhydrous THF at 100° C. is added n-butyllithium (3.3 equiv.). After one hour, a solution of Bu3SnCl (excess) is added. Other tri-alkyl-Sn compounds may be used in place of Bu3SnCl. The solution is warmed to 0° C. and quenched by the addition of saturated NH4Cl. Extractive work-up into diethyl ether affords the desired product.

Workup

  1. customquenched by the addition of saturated NH4Cl

Sources & evidence

ORD record
ord-8d6a0ff5d8ad44bbb35fe707a80aa4e4
Source dataset
uspto-grants-1993_06
Patent number
US05217705

Reaction notes

Loading…