Methanol → 5-(Phenylmethyl)-1H-pyrrole-2-carboxylic acid

HRID 1182521Notes

Reaction equation

[CH2:1]([C:8]1[NH:12][C:11]([C:13](N[C@H](C(NC(C=O)CC(O)=O)=O)C)=[O:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[K+].[Br-].C[OH:31]>>[CH2:1]([C:8]1[NH:12][C:11]([C:13]([OH:14])=[O:31])=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 887Methanol

HCID 253877Potassium Bromide

HCID 22875484HCID 22875484, compound

Product 1

HCID 184690125-(Phenylmethyl)-1H-pyrrole-2-carboxylic acid

Procedure

3-[N-(5-Benzylpyrrole-2-carbonyl)-L-alaninyl]amino-4-oxobutanoic acid (36b), was prepared (41%) from 35b by the method described for compound 36a, to afford an off white solid: mp. 109-112° C.; [α]D25 +6.3° (c 0.3, methanol); IR (KBr) 3368, 1724, 1630, 1530, 1453, 1414, 1233, 1049; 1H NMR(d4 methanol) δ 7.25-7.11 (5H, m), 6.76 (1H, d, J=3.5), 5.84 (1H, d, J=3.5), 4.51 (1H, m), 4.43 (1H, q, J=7.1), 4.23 (1H, m), 2.5 (2H, m),1.35 (3H, d, J=7.0). Anal. Calcd for C19H21N3O5. 1.75H2O: C, 56.64; H, 6.13; N, 10.43. Found: C, 56.34; H, 5.72; N, 10.00.

Workup

customto afford an off white solid

Sources & evidence

ORD record: ord-bd57d2a5a128447db7f44a97bce24dab
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07288624B2

Reaction notes

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