N-(1(S)-benzyl-2-hydroxyethyl)-3(R)-(3-(biphenyl-4-yI)-1H-pyrrol-1-yl)succinamic acid benzyl ester → 3(R)-[3-(biphenyl-4-yl)-1H-pyrrol-1-yl]-N-(2(R)-hydroxycyclohex-1(R)-yl)succinamic acid benzyl ester

HRID 566748Notes

Reaction equation

HRID 566748 reaction equation
C(OC(=O)C[C@@H](N1C=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[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.[CH2:43]([O:50][C:51](=[O:72])[CH2:52][C@@H:53]([NH:64][C:65](OC(C)(C)C)=O)[C:54]([NH:56][C@@H:57]1[CH2:62][CH2:61][CH2:60][CH2:59][C@H:58]1[OH:63])=[O:55])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1.C1(C2C=CC=CC=2)C=CC(C2CC(OC)OC2OC)=CC=1>C(O)(=O)C>[CH2:43]([O:50][C:51](=[O:72])[CH2:52][C@@H:53]([N:64]1[CH:65]=[CH:26][C:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:32][CH:31]=2)=[CH:28]1)[C:54]([NH:56][C@@H:57]1[CH2:62][CH2:61][CH2:60][CH2:59][C@H:58]1[OH:63])=[O:55])[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

5

Reactant 3

HCID 15459663N-(1(S)-benzyl-2-hydroxyethyl)-3(R)-(3-(biphenyl-4-yI)-1H-pyrrol-1-yl)succinamic acid benzyl esterHCID 183803263-Biphenyl-4-yl-2,5-dimethoxytetrahydrofuranHCID 538081083(R)-t-butoxycarbonylamino-N-(2(R)-hydroxycyclohex-1(R)-yl)succinamic acid benzyl ester

Product 1

HCID 154596733(R)-[3-(biphenyl-4-yl)-1H-pyrrol-1-yl]-N-(2(R)-hydroxycyclohex-1(R)-yl)succinamic acid benzyl esterYield 41%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

As described in Example 1(a) for the preparation of N-(1(S)-benzyl-2-hydroxyethyl)-3(R)-(3-(biphenyl-4-yl)-1H-pyrrol-1-yl)succinamic acid benzyl ester, 3(R)-t-butoxycarbonylamino-N-(2(R)-hydroxycyclohex-1(R)-yl)succinamic acid benzyl ester and 3-biphenyl-4-yl-2,5-dimethoxy-tetrahydrofuran (prepared as described in Example 1(a)) were condensed in acetic acid to furnish in 41% yield 3(R)-[3-(biphenyl-4-yl)-1H-pyrrol-1-yl]-N-(2(R)-hydroxycyclohex-1(R)-yl)succinamic acid benzyl ester as an amorphous off-white solid. 1H NMR (CDCl3): δ 7.63-7.54 (m, 6H), 7.45 (t, 2H, J=7.5 Hz), 7.36-7.26 (m, 6H), 7.06 (s, 1H), 6.76 (t, 1H, J=2.4 Hz), 6.58 (s, 1H), 5.46 (d, 1H, J=7.0 Hz), 5.15-5.10 (m, 3H), 3.61-3.55 (m, 1H), 3.49 (dd, 1H, J=5.5, 16.6 Hz), 3.27-3.21 (m, 1H), 3.06 (dd, 1H, J=8.3, 16.7 Hz), 2.04-1.98 (m, 1H), 1.85-1.78 (m, 1H), 1.71-1.51 (m, 2H), 1.32-1.02 (m, 4H). Anal. Calculated for C33H34N2O4•H2O:C, 73.31; H, 6.71; N, 5.18. Found: C, 72.93; H, 6.72; N, 4.93.

Sources & evidence

ORD record
ord-df641899316f4462a2160ac322e8e139
Source dataset
uspto-grants-2001_01
Patent number
US06174915B1

Reaction notes

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