N-(1(S)-benzyl-2-hydroxyethyl)-3(R)-[3-(4'-cyano-biphenyl4-yl)-1H-pyrrol-1-yl]succinamic acid benzyl ester → 3(R)-[3-(4'-carbamoylbiphenyl-4-yl)-1H-pyrrol-1-yl]-N-(1(S)-hydroxymethyl-2,2-dimethyl-propyl)succinamic acid benzyl ester

HRID 382159Notes

Reaction equation

HRID 382159 reaction equation
C(OC(=O)C[C@@H](N1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][C:39]([C:42]#[N:43])=[CH:38][CH:37]=3)=[CH:32][CH:31]=2)=[CH:26]1)C(N[C@@H](CC1C=CC=CC=1)CO)=O)C1C=CC=CC=1.FC(F)(F)C(O)=[O:48].[CH2:52]([O:59][C:60](=[O:74])[CH2:61][C@@H:62]([NH2:73])[C:63]([NH:65][CH:66]([CH2:71][OH:72])[C:67]([CH3:70])([CH3:69])[CH3:68])=[O:64])[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>ClCCCl>[CH2:52]([O:59][C:60](=[O:74])[CH2:61][C@@H:62]([N:73]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][C:39]([C:42](=[O:48])[NH2:43])=[CH:38][CH:37]=3)=[CH:32][CH:31]=2)=[CH:26]1)[C:63]([NH:65][C@H:66]([CH2:71][OH:72])[C:67]([CH3:70])([CH3:69])[CH3:68])=[O:64])[C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1

Participants

4

Reactant 2

HCID 15459675N-(1(S)-benzyl-2-hydroxyethyl)-3(R)-[3-(4'-cyano-biphenyl4-yl)-1H-pyrrol-1-yl]succinamic acid benzyl esterHCID 701438803(r)-Amino-n-(1-hydroxymethyl-2,2-dimethyl-propyl)succinamic acid benzyl ester trifluoroacetate salt

Product 1

HCID 700994053(R)-[3-(4'-carbamoylbiphenyl-4-yl)-1H-pyrrol-1-yl]-N-(1(S)-hydroxymethyl-2,2-dimethyl-propyl)succinamic acid benzyl esterYield 41%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

As described for Example 4(a) for the preparation of N-(1(S)-benzyl-2-hydroxyethyl)-3(R)-[3-(4′-cyano-biphenyl4-yl)-1H-pyrrol-1-yl]succinamic acid benzyl ester, crude 3-(4′-carboxamidobiphenyl)-2,5-dimethoxy-tetrahydrofuran and 3(R)-amino-N-(1-hydroxymethyl-2,2-dimethyl-propyl)succinamic acid benzyl ester trifluoroacetate salt were condensed in 1,2-dichloroethane to furnish 110 mg (41%) of 3(R)-[3-(4′-carbamoylbiphenyl-4-yl)-1H-pyrrol-1-yl]-N-(1(S)-hydroxymethyl-2,2-dimethyl-propyl)succinamic acid benzyl ester as a solid, mp 201-3° C.

Sources & evidence

ORD record
ord-2349ce39468d42688ae27d3a6748f493
Source dataset
uspto-grants-2001_10
Patent number
US06306892B1

Reaction notes

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