6-Phenylhexanoic Acid → (RS)-5-(4-Benzyloxy-phenyl)-4-(6-phenyl-hexanoylamino)-pentanoic acid ethyl ester

HRID 852883

Reaction equation

HRID 852883 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15]([O:17][C:18](=[O:45])[CH:19]=[CH:20][CH:21]([NH:37]C(OC(C)(C)C)=O)[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:25][CH:24]=1)[CH3:16]>>[CH2:15]([O:17][C:18](=[O:45])[CH2:19][CH2:20][CH:21]([NH:37][C:12](=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:25][CH:24]=1)[CH3:16]

Participants

3

Reactant 2

HCID 796956-Phenylhexanoic AcidHCID 69416006(RS)-5-(4-Benzyloxy-phenyl)-4-tertbutoxycarbonylamino-pent-2-enoic acid ethyl ester

Product 1

HCID 69416793(RS)-5-(4-Benzyloxy-phenyl)-4-(6-phenyl-hexanoylamino)-pentanoic acid ethyl ester

Procedure

From 6-phenylhexanoic acid 71a and (RS)-5-(4-Benzyloxy-phenyl)-4-tertbutoxycarbonylamino-pent-2-enoic acid ethyl ester 77 (83% yield): 1H nmr (CDCl3) δ 1.26 (t, J=7.2 Hz, 3H), 1.28-1.90 (m, 9H), 2.11 (t, J=7.4 Hz, 2H), 2.29-2.38 (m, 2H), 2.60 (t, J=7.6 Hz, 2H), 2.71-2.77 (m, 2H), 4.12 (q, J=7.1 Hz, 2H), 5.03 (s, 2H), 5.55 (br d, J=8.7 Hz, 1H), 6.91 (d, J=8.6 Hz, 2H), 7.10 (d, J=8.6 Hz, 2H), 7.16-7.44 (m, 10H). 13C nmr (CDCl3) δ 173.8, 172.8, 157.5, 142.4, 136.9, 130.3, 129.9, 128.5, 128.3, 128.2, 127.8, 127.4, 125.6, 114.7, 69.9, 60.5, 50.1, 40.3, 36.7, 35.6, 31.1, 31.0, 28.7, 28.6, 25.5, 14.1.

Sources & evidence

ORD record
ord-1c4b57f4be704b7990ebe08c4468406f
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Linked notes

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