Acetic Acid → Boc-Thr(Bzl)-Pro-OH

HRID 2419487Notes

Reaction equation

HRID 2419487 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].CCN(CC)CC.[NH:16]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C@H:17]([C:28](ON1C(=O)CCC1=O)=[O:29])[C@@H:18]([CH3:27])[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(O)(=O)C>CN(C=O)C.C(Cl)(Cl)Cl.CCOC(C)=O>[NH:16]([C:38]([O:40][C:41]([CH3:42])([CH3:44])[CH3:43])=[O:39])[C@H:17]([C:28]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])=[O:29])[C@@H:18]([CH3:27])[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 145742L-ProlineHCID 12879029Boc-Thr(Bzl)-OSu

Product 1

HCID 13091018Boc-Thr(Bzl)-Pro-OH

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of H-Pro-OH (1.0 g, 8.69 mmol) in DMF (15 ml) was stirred with Et3N (2.44 ml) and Boc-Thr(Bzl)-OSu (3.88 g, 9.56 mmol) at 0° C for 1 hr and 25° C for 72 hrs. The reaction was acidified to pH 3 with acetic acid and worked up as described in Example 2 to produce a crystalline product from EtOAc and petroleum ether: 3.0 g (85.0%); mp 84°-88° C; [α]D25 -52.2° (c 1, CHCl3). Anal. Calcd for C21H30N2O6 (406.48): C, 62.05; H, 7.43; N, 6.89. Found: C, 62.29; H, 7.52; N, 6.86.

Sources & evidence

ORD record
ord-a41cc474166247838ae241115658918c
Source dataset
uspto-grants-1978_08
Patent number
US04105652

Reaction notes

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